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

HRID 1157496Notes

Reaction equation

HRID 1157496 reaction equation
[C:1]([CH2:9][NH:10][CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:26]([O:28][CH2:29]C)=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(N[C@H](CC1C=CC(C2C=CC=C(CNC)C=2)=CC=1)C(OC)=O)=O)(C)(C)C>>[C:1]([CH2:9][NH:10][CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C@@H:25]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:26]([O:28][CH3:29])=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 69685372ethyl (S)-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-tert-butoxycarbonylaminopropionateHCID 86601624methyl (R)-2-tert-butoxycarbonylamino-3-(3'-methylaminomethylbiphenyl-4-yl)propionate

Product 1

HCID 69686257methyl (R)-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-tert-butoxycarbonylaminopropionateYield 85%

Procedure

In a manner similar to the preparation of ethyl (S)-3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-tert-butoxycarbonylaminopropionate (Example 28e), using 5.0 g of methyl (R)-2-tert-butoxycarbonylamino-3-(3′-methylaminomethylbiphenyl-4-yl)propionate, 5.6 g of desired amide are obtained with an 85% yield.

Workup

  1. customare obtained with an 85% yield

Sources & evidence

ORD record
ord-11e9fd8d98ed429f8fa14e9966b3334e
Source dataset
uspto-grants-2010_10
Patent number
US07807669B2

Reaction notes

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