(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid → 2-{2-[(Azepane-1-carbonyl)-amino]-4-methyl-pentanoylamino}-3-(4-benzyloxy-phenyl)-propionic acid methyl ester

HRID 2230306Notes

Reaction equation

HRID 2230306 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.[CH3:19][O:20][C:21](=[O:33])[C@@H:22]([NH2:32])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>C(OCC)(=O)C>[CH3:19][O:20][C:21](=[O:33])[CH:22]([NH:32][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])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acidHCID 10856719O-Methyl-L-tyrosine methyl ester

Product 1

HCID 700604322-{2-[(Azepane-1-carbonyl)-amino]-4-methyl-pentanoylamino}-3-(4-benzyloxy-phenyl)-propionic acid methyl esterYield 151%

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 methyl ester (Bachem, 0.277 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 (0.34 g, 83%), mp=72-74° C.

Workup

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

Sources & evidence

ORD record
ord-065f830b14d44c96a61887b5f7fc3078
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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