(S)-2-Cyclopentyloxycarbonylamino-3,3-dimethyl-butyric acid → (5S,8S)-methyl-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate

HRID 2038563

Reaction equation

HRID 2038563 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:21][C@:8]2([O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[CH2:9]2)[CH2:7][NH:6]1)=[O:4].[CH:22]1([O:27][C:28]([NH:30][C@@H:31]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:32](O)=[O:33])=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:21][C@:8]2([O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[CH2:9]2)[CH2:7][N:6]1[C:32](=[O:33])[C@@H:31]([NH:30][C:28]([O:27][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:29])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:4]

Participants

3

Reactant 2

HCID 23595129(S)-2-Cyclopentyloxycarbonylamino-3,3-dimethyl-butyric acidHCID 59547337HCID 59547337, compound

Product 1

HCID 59547346(5S,8S)-methyl-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylateYield 42.3%

Procedure

Following the same procedure as Example 1 step G using (5S,8S)-methyl-3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (30 mg, 97 μmol) and (S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoic acid (28 mg, 116 μmol, 1.2 eq.) gave 22 mg (41 μmol) of (5S,8S)-methyl-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (C3). 1H NMR (300 MHz, CDCl3) 7.35-6.8 (m, 4H), 5.21-5.06 (m, 1H), 4.86 (m, 1H), 4.55-3.56 (m, 8H), 2.65-2.48 (m, 1H), 2.0 (m, 1H), 1.7-1.1 (m, 9H), 0.9-0.7 (m, 9H).

Sources & evidence

ORD record
ord-d14fc31833cc468388cbe040e7f57689
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Linked notes

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