(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamide → HCID 59547311, compound

HRID 2038560Notes

Reaction equation

HRID 2038560 reaction equation
[CH:1]1([CH2:7][C:8]([NH:10][C@@H:11]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:12]([N:14]2[C@H:29]([C:30]([OH:32])=O)[CH2:28][C@@:16]3([O:20][C:19](=[O:21])[N:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17]3)[CH2:15]2)=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]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:1]1([CH2:7][C:8]([NH:10][C@@H:11]([C:33]([CH3:35])([CH3:36])[CH3:34])[C:12]([N:14]2[C@H:29]([C:30]([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])=[O:32])[CH2:28][C@@:16]3([O:20][C:19](=[O:21])[N:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17]3)[CH2:15]2)=[O:13])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 23634853(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 59547343HCID 59547343, compound

Product 1

HCID 59547311HCID 59547311, compoundYield 30.6%

Procedure

Following the same procedure as Example 1 step 9 using (5R,8S)-7-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-2-oxo-3-phenyl-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylic acid (49 mg, 98 μmol) and (3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide (31 mg, 137 μmol, 1.4 eq.) gave 20 mg (30 μmol) of (5R,8S)-7-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-N-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)-2-oxo-3-phenyl-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxamide (G2). LC MS+/−: 668.56/666.64 at 3.24 min (10-90%, 3-5 min, Formic Acid).

Sources & evidence

ORD record
ord-4ae814965d0a440dbec06b31d409aeb3
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

Loading…