ChemInform Abstract: Efficient kg‐Scale Synthesis of Thrombin Inhibitor CRC 220.

Jendralla, H.; Seuring, B.; Herchen, J.; Kulitzscher, B.; Wunner, J.; Stueber, W.; Koschinsky, R.

doi:10.1002/chin.199609238

Cited by 6 publications

(11 citation statements)

References 1 publication

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“…Careful thought had to be given to the sequence and how high ee could be attained due to the relatively hydrolytically labile nitrile group, which is subsequently converted to the amidine moiety of 152. 201 In another example Rh-(S,S)-EtDuPhos (Rh-13b) gave high enantioselectivity (>98%) with the fluorosubstituted amino esters 154a-c even though the substrates were E/Z-mixtures. 202 With an additional b-substituent, b-trifluoromethyl a-amino acids can be prepared by an asymmetric reduction in the presence of Rh-TCFP (Rh-124).…”

Section: Substrate Screeningmentioning

confidence: 99%

Asymmetric homogeneous hydrogenations at scale

Ager¹,

2012

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Asymmetric hydrogenations are increasingly being used to introduce stereogenic centres into products used in the life sciences industries. There are a number of potential pitfalls when moving from a laboratory reaction to a manufacturing process, not least of which is safety. Time-to-market pressure leads to short development times, which in the past could be a large barrier for the implementation of catalytic steps; now there are new ways to minimise this problem. The potential problems associated with impurities and other methods that can shut down the hydrogenation reactions are highlighted in this critical review (353 references).

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Section: Substrate Screeningmentioning

confidence: 99%

Asymmetric homogeneous hydrogenations at scale

Ager¹,

2012

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“…Precipitation from the reaction mixture increased the selectivity to > 99.8% ee; this process has been scaled up to 10 kg (Scheme 1.16 ) [120] .…”

Section: Synthesis Of Pharmaceutical Intermediatesmentioning

confidence: 99%

Reduction of Functionalized Alkenes

Genêt

2008

Modern Reduction Methods

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“…Reaction of 6 with hydroxylamine in ethanol at low temperature furnished the desired amidoxime 7 in excellent yield. The nitrile to amidoxime transformation is routinely performed at reflux 22 , however, we found that reaction of 6 with hydroxylamine at temperatures above 0°C resulted in benzyl ester cleavage.…”

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confidence: 90%

2-Amidino analogs of glycine–amiloride conjugates: Inhibitors of urokinase-type plasminogen activator

Massey

Harley

Pasupuleti

et al. 2012

Bioorganic & Medicinal Chemistry Letters

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The relative non-toxicity of the diuretic amiloride, coupled with its selective inhibition of the protease urokinase plasminogen activator (uPA), makes this compound class attractive for structure-activity studies. Herein we substituted the C(2)-acylguanidine of C(5)-glycyl-amiloride with amidine and amidoxime groups. The data show the importance of maintaining C(5)-hydrophobicity. The C(5)-benzylglycine analogs containing either C(2)-acylguanidine or amidine inhibited uPA with an IC50 ranging from 3 to 7μM and were cytotoxic to human U87 malignant glioma cells.

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ChemInform Abstract: Efficient kg‐Scale Synthesis of Thrombin Inhibitor CRC 220.

Cited by 6 publications

References 1 publication

Asymmetric homogeneous hydrogenations at scale

Asymmetric homogeneous hydrogenations at scale

Reduction of Functionalized Alkenes

2-Amidino analogs of glycine–amiloride conjugates: Inhibitors of urokinase-type plasminogen activator

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