(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamide → HCID 59547324, compound

HRID 2038568Notes

Reaction equation

HRID 2038568 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]([OH:19])=O)[N:14]([C:20](=[O:36])[C@@H:21]([NH:26][C:27](=[O:35])[CH2:28][CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:13]3)[O:10][C:9]2=[O:37])[CH:5]=[CH:6][CH:7]=1.[NH2:38][C@@H:39]([CH2:48][CH2:49][CH3:50])[CH:40]([OH:47])[C:41]([NH:43][CH:44]1[CH2:46][CH2:45]1)=[O:42]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@:11]3([CH2:16][C@@H:15]([C:17]([NH:38][C@@H:39]([CH2:48][CH2:49][CH3:50])[CH:40]([OH:47])[C:41]([NH:43][CH:44]4[CH2:45][CH2:46]4)=[O:42])=[O:19])[N:14]([C:20](=[O:36])[C@@H:21]([NH:26][C:27](=[O:35])[CH2:28][CH:29]4[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]4)[C:22]([CH3:25])([CH3:23])[CH3:24])[CH2:13]3)[O:10][C:9]2=[O:37])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 23634853(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 59547299HCID 59547299, compound

Product 1

HCID 59547324HCID 59547324, compoundYield 63.6%

Procedure

Following the procedure from Example 1 step I using (5R,8S)-3-(3-chlorophenyl)-7-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylic acid (D4) (12 mg, 22 μmol) and (3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide (7.3 mg, 33 μmol) gave 10 mg (14 μmol) of (5R,8S)-3-(3-chlorophenyl)-7-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-N-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxamide (E4). LC MS+/−: 702.54/700.74 at 3.68 min (10-90%, 3-5 min, Formic Acid).

Sources & evidence

ORD record
ord-6bbc53d4476c4541a27836f78ed37643
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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