ethyl (S)-2-tert-butoxycarbonylamino-3-(3'-methylaminomethylbiphenyl-4-yl)propionate → methyl (R)-2-tert-butoxycarbonylamino-3-(3'-methylaminomethylbiphenyl-4-yl)propionate

HRID 271858Notes

Reaction equation

HRID 271858 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][CH3:30])[CH:23]=2)=[CH:18][CH:17]=1)[C:10]([O:12][CH2:13]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC([C@@](N)(CC1C=CC(C2C=CC=C(C=O)C=2)=CC=1)C(OC)=O)=O)(C)(C)C>>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][CH3:30])[CH:23]=2)=[CH:20][CH:21]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 69685901ethyl (S)-2-tert-butoxycarbonylamino-3-(3'-methylaminomethylbiphenyl-4-yl)propionateHCID 86601625methyl (R)-2-tert-butoxycarbonyl-amino-3-(3'-formylbiphenyl-4-yl)propionate

Product 1

HCID 86601624methyl (R)-2-tert-butoxycarbonylamino-3-(3'-methylaminomethylbiphenyl-4-yl)propionateYield 50%

Procedure

In a manner similar to the preparation of ethyl (S)-2-tert-butoxycarbonylamino-3-(3′-methylaminomethylbiphenyl-4-yl)propionate (Example 28d) using 10.2 g (26.6 mmol) of methyl (R)-2-tert-butoxycarbonyl-amino-3-(3′-formylbiphenyl-4-yl)propionate, 5.0 g of expected amine are isolated with a 50% yield.

Workup

  1. customare isolated with a 50% yield

Sources & evidence

ORD record
ord-e58cab58ab3b42778f2bb30ce01d7501
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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