HCID 6452452, compound → HCID 70059967, compound

HRID 2230307Notes

Reaction equation

HRID 2230307 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:36])[C@@H:22]([NH2:35])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:26][CH:25]=1>C(OCC)(=O)C.CCCCCC>[CH3:19][O:20][C:21](=[O:36])[CH:22]([NH:35][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][C:31]([CH3:32])([CH3:33])[CH3:34])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 6452452HCID 6452452, compoundHCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid

Product 1

HCID 70059967HCID 70059967, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

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-tert-butoxy-phenyl)-propionic acid methyl ester (Bachem, 0.247 g, 0.86 mmol) were coupled according to the procedure described in Example 42. The residue was passed through a plug of silica gel eluting with 70% ethyl acetate/hexane. The material obtained was purified by crystallization from hot hexane/ethyl acetate to give the title compound as a white solid (0.31 g, 81%), mp=96-99° C.

Workup

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

Sources & evidence

ORD record
ord-c7c06fce343d43c3ab11a9b31a07b0b9
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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