N-Carbobenzoxy-L-valine → Z-Val-Tyr(But)-O-CH(CH3)2

HRID 904970Notes

Reaction equation

HRID 904970 reaction equation
[NH2:1][C@H:2]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.Cl.[NH:22]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:23]([C:27](O)=[O:28])[CH:24]([CH3:26])[CH3:25]>CO>[NH:22]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:23]([C:27]([NH:1][C@H:2]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[CH:8][CH:9]=1)=[O:28])[CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 726987N-Carbobenzoxy-L-valineHCID 131713301H-Tyr(But)-O-CH(CH3)2 hydrochloride

Product 1

HCID 131713303Z-Val-Tyr(But)-O-CH(CH3)2

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.9 g (25 mmoles) of H-Tyr(But)-O-CH(CH3)2 hydrochloride and 6.27 g (25 mmoles) of Z-Val-OH are subjected to a condensation reaction analogously to Example 30 C. Yield 11.8 g (92%), melting point 133°-134°, [α]D26 =-25.2° (c=1, methanol).

Sources & evidence

ORD record
ord-de9a3ebc50ca48e499d15bd40f32ed0b
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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