[(R)-3-(3-Acetylaminopyridin-2-yl)-1-(2,5-difluorobenzyl)-2-oxopropyl)carbamic acid tert-butyl ester → HCID 66639371, compound

HRID 1094470Notes

Reaction equation

[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]([CH2:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[F:30])[C:9](=[O:21])[CH2:10][C:11]1[C:16]([NH:17][C:18](=[O:20])[CH3:19])=[CH:15][CH:14]=[CH:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Li+]>>[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]([CH2:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[F:30])[C@@H:9]([OH:21])[CH2:10][C:11]1[C:16]([NH:17][C:18](=[O:20])[CH3:19])=[CH:15][CH:14]=[CH:13][N:12]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 66639630[(R)-3-(3-Acetylaminopyridin-2-yl)-1-(2,5-difluorobenzyl)-2-oxopropyl)carbamic acid tert-butyl ester

HCID 131729497Lithium triacetyloxyboranuide

Product 1

HCID 66639371HCID 66639371, compound

Procedure

Using general procedure 3 with [(R)-3-(3-Acetylaminopyridin-2-yl)-1-(2,5-difluorobenzyl)-2-oxopropyl]carbamic acid tert-butyl ester (1.68 mmol; 729.00 mg) and lithium triacetoxyborohydride (8.41 mmol; 2.22 g) as the reducing agent gives the title compound.

Sources & evidence

ORD record: ord-2d040c4d29804a7195a1631d4bcd5186
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133907B2

Reaction notes

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