(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid → HCID 70060021, compound

HRID 2230305Notes

Reaction equation

HRID 2230305 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.[CH2:19]([O:26][C:27](=[O:39])[C@@H:28]([NH2:38])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C>[CH2:19]([O:26][C:27](=[O:39])[CH:28]([NH:38][C:12](=[O:14])[CH: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])[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][CH2:37][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:34][CH:35]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acidHCID 15042588O-Methyl-L-tyrosine phenylmethyl ester

Product 1

HCID 70060021HCID 70060021, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product from Example Z (2(S)-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid) (0.20 g, 0.78 mmol) and 2(S)-amino-3-(4-methoxy-phenyl)-propionic acid benzyl ester (Bachem, 0.459 g, 0.86 mmol) were coupled according to the procedure described in Example 3. The residue was passed through a plug of silica gel eluting with ethyl acetate. The material obtained was purified by crystallization from hot hexane/ethyl acetate to give the title compound as a white solid (0.2 g, 43%), mp=99-101° C.

Workup

  1. customThe material obtained
  2. customwas purified by crystallization from hot hexane/ethyl acetate

Sources & evidence

ORD record
ord-6159a6a27b9f4f7e8de2bb23130c0087
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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