Ammonia methanol → [(RS)-1-(6-Bromo-pyridin-2-yl)-2-((R)-1-carbamoyl-2,2,2-trifluoro-1-methyl-ethoxy)-1-methyl-ethyl]-carbamic acid tert-butyl ester

HRID 538314Notes

Reaction equation

C([O:3][C:4](=O)[C@:5]([O:11][CH2:12][C:13]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[N:24]=1)([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:14])([CH3:10])[C:6]([F:9])([F:8])[F:7])C.[NH3:31].CO>>[C:19]([O:18][C:16](=[O:17])[NH:15][C:13]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[N:24]=1)([CH3:14])[CH2:12][O:11][C@@:5]([C:4](=[O:3])[NH2:31])([CH3:10])[C:6]([F:7])([F:8])[F:9])([CH3:20])([CH3:22])[CH3:21]

Participants

Reactant 2

HCID 21705897Ammonia methanol

HCID 86715547(R)-2-[(RS)-2-(6-Bromo-pyridin-2-yl)-2-tert-butoxycarbonylamino-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid ethyl ester

Product 1

HCID 86715546[(RS)-1-(6-Bromo-pyridin-2-yl)-2-((R)-1-carbamoyl-2,2,2-trifluoro-1-methyl-ethoxy)-1-methyl-ethyl]-carbamic acid tert-butyl ester

Procedure

A solution of (R)-2-[(RS)-2-(6-bromo-pyridin-2-yl)-2-tert-butoxycarbonylamino-propoxy]-3,3,3-tri-fluoro-2-methyl-propionic acid ethyl ester (3.0 g, 6.01 mmol) in 7N NH3/MeOH (6.5 ml) was stirred in a sealed glass vial at 55° C. for 72 h. The reaction mixture was concentrated to leave the title compound as a colourless solid that was used in the next step without further purification. HPLC RtH4=1.12, 1.14 min (diastereomers); ESIMS: 470, 472 [(M+H)+].

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-fb9a61f89a4249b88c32aabb003410d4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865712B2

Reaction notes

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