Carbamic acid, [[(3R,4R)-4-(trifluoromethyl)-3-pyrrolidinyl]methyl]-, 1,1-dimethylethyl ester, rel- → HCID 58748306, compound

HRID 1162694Notes

Reaction equation

HRID 1162694 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C@H:9]1[C@H:13]([C:14]([F:17])([F:16])[F:15])[CH2:12][NH:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[N+](C1C=CC([O:28][C:29](=O)[NH:30][C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]3=[O:43])=[CH:33][C:32]=2[F:44])=CC=1)([O-])=O>>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C@H:9]1[C@H:13]([C:14]([F:15])([F:16])[F:17])[CH2:12][N:11]([C:29](=[O:28])[NH:30][C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]3=[O:43])=[CH:33][C:32]=2[F:44])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 57429455Carbamic acid, [[(3R,4R)-4-(trifluoromethyl)-3-pyrrolidinyl]methyl]-, 1,1-dimethylethyl ester, rel-HCID 58748307[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-carbamic acid 4-nitro-phenyl ester

Product 1

HCID 58748306HCID 58748306, compound

Procedure

77.1 Using general procedure H, (3S,4S)-(4-trifluoromethyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester (H. Fukui et al., Bioorganic & Medicinal Chemistry Letters, 1998, 8, 2833) was coupled with [2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-carbamic acid 4-nitro-phenyl ester (prepared according to example 54.3) to give {(3R,4S)-1-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-4-trifluoromethyl-pyrrolidin-3-ylmethyl}-carbamic acid tert-butyl ester. Orange oil. MS 499.3 ([M+H]+)

Sources & evidence

ORD record
ord-8ee0758bca354aaa91e2ec37d7326875
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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