ethyl (S)-2-amino-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}propionate → methyl (R)-2-amino-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}propionate

HRID 271860Notes

Reaction equation

HRID 271860 reaction equation
[NH2:1][C@@H:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][CH2:23][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:16]=2)=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6]C)=[O:4].C(CNCC1C=C(C2C=CC(C[C@@H](NC(OC(C)(C)C)=O)C(OC)=O)=CC=2)C=CC=1)(=O)C1C=CC=CC=1>>[NH2:1][C@H:2]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][CH2:23][C:24](=[O:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:16]=2)=[CH:13][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

3

Reactant 2

HCID 69685681ethyl (S)-2-amino-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}propionateHCID 69686257methyl (R)-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-tert-butoxycarbonylaminopropionate

Product 1

HCID 69686251methyl (R)-2-amino-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}propionateYield 92%

Procedure

In a manner similar to the preparation of ethyl (S)-2-amino-3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}propionate (Example 28f), using 5.6 g of methyl (R)-3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-tert-butoxycarbonylaminopropionate, 4.1 g of amine are obtained with a 92% yield.

Workup

  1. customare obtained with a 92% yield

Sources & evidence

ORD record
ord-04816dd57ff44fdd940befef2ab99b13
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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