(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamide → Cyclopentyl-(2s)-1-((5s,8s)-3-(3-chlorophenyl)-8-((3s)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonan-7-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

HRID 2038565Notes

Reaction equation

HRID 2038565 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@@:11]3([CH2:16][C@@H:15]([C:17](O)=[O:18])[N:14]([C:20](=[O:35])[C@@H:21]([NH:26][C:27]([O:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:28])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:13]3)[O:10][C:9]2=[O:36])[CH:5]=[CH:6][CH:7]=1.[NH2:37][C@@H:38]([CH2:47][CH2:48][CH3:49])[CH:39]([OH:46])[C:40]([NH:42][CH:43]1[CH2:45][CH2:44]1)=[O:41]>>[CH:30]1([O:29][C:27](=[O:28])[NH:26][C@@H:21]([C:22]([CH3:25])([CH3:23])[CH3:24])[C:20]([N:14]2[C@H:15]([C:17](=[O:18])[NH:37][C@@H:38]([CH2:47][CH2:48][CH3:49])[CH:39]([OH:46])[C:40]([NH:42][CH:43]3[CH2:44][CH2:45]3)=[O:41])[CH2:16][C@:11]3([O:10][C:9](=[O:36])[N:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[CH2:12]3)[CH2:13]2)=[O:35])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 23634853(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 59547318(5S,8S)-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylic acid

Product 1

HCID 131731031Cyclopentyl-(2s)-1-((5s,8s)-3-(3-chlorophenyl)-8-((3s)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonan-7-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamateYield 36%

Procedure

Following the same procedure as Example 1 step 1 using (5S,8S)-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylic acid (D3) (10 mg, 20 μmol) and (3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide (7 mg, 28 μmol) gave 5 mg (7.2 μmol) of Cyclopentyl-(2S)-1-((5S,8S)-3-(3-chlorophenyl)-8-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonan-7-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (E3). LC MS+: 690.38 at 3.31 min (10-90%, 3-5 min, Formic Acid).

Sources & evidence

ORD record
ord-0de9c4868afc44159980a14fab048887
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

Loading…