(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid → HCID 70058836, compound

HRID 2230302Notes

Reaction equation

[N:1]1([C:8]([NH:10][C@@H:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([OH:14])=O)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([O:23][C:24](=[O:43])[C:25]([NH2:42])([CH3:41])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:29][CH:28]=1)([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24](=[O:43])[C@@:25]([NH:42][C:12](=[O:14])[C@@H:11]([NH:10][C:8]([N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:9])[CH2:15][CH:16]([CH3:18])[CH3:17])([CH3:41])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:29][CH:28]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

Reactant 2

HCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid

HCID 70059389HCID 70059389, compound

Product 1

HCID 70058836HCID 70058836, compoundYield 38%

Procedure

A solution of the product from Example Z ((2S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid) (0.5 g, 1.95 mmol) and the product from Example D (2-amino-2-methyl-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (0.73 g, 2.15 mmol) were coupled according to the procedure described in Example 3. The two diastereomeric products were separated by chromatography (silica gel, 1:1 heptane/EtOAc) to give a high Rf product as a white solid (0.43 g, 38%), mp=46-49° C.

Workup

customThe two diastereomeric products were separated by chromatography (silica gel, 1:1 heptane/EtOAc)

Sources & evidence

ORD record: ord-689eeae190c84aa3b82e3d84032a722c
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06423689B1

Reaction notes

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