2(S)-[(4-methyl-piperazine-1-carbonyl)-amino]-4-methyl-pentanoic acid → 3-(4-Benzyloxy-phenyl)-2-{4-methyl-2-[(4-methyl-piperazine-1-carbonyl)-amino]-pentanoylamino}-propionic acid tert-butyl ester

HRID 2230300Notes

Reaction equation

HRID 2230300 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][C@@H:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([OH:14])=O)=[O:9])[CH2:4][CH2:3]1.[C:19]([O:23][C:24](=[O:42])[C@@H:25]([NH2:41])[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:42])[CH:25]([NH:41][C:12](=[O:14])[CH:11]([NH:10][C:8]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)=[O:9])[CH2:15][CH:16]([CH3:18])[CH3:17])[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

3

Reactant 2

HCID 9390592(S)-[(4-methyl-piperazine-1-carbonyl)-amino]-4-methyl-pentanoic acidHCID 11151579tert-butyl (2S)-2-amino-3-[4-(benzyloxy)phenyl]propanoate

Product 1

HCID 700611733-(4-Benzyloxy-phenyl)-2-{4-methyl-2-[(4-methyl-piperazine-1-carbonyl)-amino]-pentanoylamino}-propionic acid tert-butyl esterYield 60%

Procedure

A solution of the product from Example AF (2(S)-[(4-methyl-piperazine-1-carbonyl)-amino]-4-methyl-pentanoic acid) (0.25 g, 1.03 mmol) and the product from Example A ((S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (0.35 g, 1.03 mmol) were coupled according to the procedure described in Example AH. The reaction mixture was purified by chromatography (silica gel, gradient elution 1:1 EtOAc/heptane; 9:1 EtOAc/EtOH; 9:1:0.1 EtOAc/EtOH/NH4OH) to give the title compound as a white foam (0.35 g, 60%).

Workup

  1. customThe reaction mixture was purified by chromatography (silica gel, gradient elution 1:1 EtOAc/heptane; 9:1 EtOAc/EtOH; 9:1:0.1 EtOAc/EtOH/NH4OH)

Sources & evidence

ORD record
ord-d36c7870f40a41ceb9d286e6a1386798
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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