An efficient chiral synthesis of (R)-N-[3-acetyl-4-(2-hydroxy-3-isopropylamino-propoxy)phenyl]-butanamide with high enantioselectivity

Wang, Nai‐Xing; Tang, Xinliang

doi:10.1007/s11426-009-0116-x

Cited by 2 publications

(2 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Generally, the cardioselectivity and β‐blocking activity of S ‐enantiomers of aryloxypropanol amine is 50–500 times more than the R ‐enantiomers. Several strategies for the synthesis of acebutolol have been reported in the literature (Scheme ) …”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Biocatalytic Approach for the Synthesis of Enantiopure Acebutolol as a β₁‐Selective Blocker

et al. 2015

View full text Add to dashboard Cite

A new chemoenzymatic route is reported to synthesize acebutolol, a selective β1 adrenergic receptor blocking agent in enantiopure (R and S) forms. The enzymatic kinetic resolution strategy was used to synthesize enantiopure intermediates (R)- and (S)-N-(3-acetyl-4-(3-chloro-2-hydroxypropoxy)phenyl)butyramide from the corresponding racemic alcohols. The results showed that out of eleven commercially available lipase preparations, two enzyme preparations (Lipase A, Candida antarctica, CLEA [CAL CLEA] and Candida rugosa lipase, 62316 [CRL 62316]) act in enantioselective manner. Under optimized conditions the enantiomeric excess of both (R)- and (S)-N-(3-acetyl-4-(3-chloro-2-hydroxypropoxy)phenyl)butyramide were 99.9 and 96.8%, respectively. N-alkylation of both the (R) and (S) intermediates with isopropylamine gave enantiomerically pure (R and S)- acebutolol with a yield 68 and 72%, respectively. This study suggests a high yielding, easy and environmentally green approach to synthesize enantiopure acebutolol.

show abstract

Section: Methodsmentioning

confidence: 99%

“…Several strategies for the synthesis of acebutolol have been reported in the literature (Scheme 1). [22][23][24][25] Only a few reports are available for the enantiopure synthesis of this drug molecule. One of the reported strategies (strategy 1) uses chiral halohydrin or glyceryl acetonide to convert phenol 3 to enantiopure halohydrin 5.…”

mentioning

confidence: 99%

Biocatalytic Approach for the Synthesis of Enantiopure Acebutolol as a β₁‐Selective Blocker

et al. 2015

View full text Add to dashboard Cite

show abstract

Single enantiomeric β-blockers—The existing technologies

Agustian

Kamaruddin

Bhatia

2010

Process Biochemistry

View full text Add to dashboard Cite

An efficient chiral synthesis of (R)-N-[3-acetyl-4-(2-hydroxy-3-isopropylamino-propoxy)phenyl]-butanamide with high enantioselectivity

Cited by 2 publications

References 20 publications

Biocatalytic Approach for the Synthesis of Enantiopure Acebutolol as a β₁‐Selective Blocker

Biocatalytic Approach for the Synthesis of Enantiopure Acebutolol as a β₁‐Selective Blocker

Single enantiomeric β-blockers—The existing technologies

Contact Info

Product

Resources

About

An efficient chiral synthesis of (R)-N-[3-acetyl-4-(2-hydroxy-3-isopropylamino-propoxy)phenyl]-butanamide with high enantioselectivity

Cited by 2 publications

References 20 publications

Biocatalytic Approach for the Synthesis of Enantiopure Acebutolol as a β1‐Selective Blocker

Biocatalytic Approach for the Synthesis of Enantiopure Acebutolol as a β1‐Selective Blocker

Single enantiomeric β-blockers—The existing technologies

Contact Info

Product

Resources

About

Biocatalytic Approach for the Synthesis of Enantiopure Acebutolol as a β₁‐Selective Blocker

Biocatalytic Approach for the Synthesis of Enantiopure Acebutolol as a β₁‐Selective Blocker