Dicyclohexylcarbodiimide → Boc-Cys(MBzl)-Phe-betaAla-OH

HRID 467356Notes

Reaction equation

HRID 467356 reaction equation
[NH:1]([C:18]([O:20]C(C)(C)C)=O)[C@H:2]([C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:25]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@H:26](C(O)=O)[CH2:27][S:28][CH2:29][C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1.C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>>[NH:25]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@H:26]([C:18]([NH:1][C@H:2]([C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:20])[CH2:27][S:28][CH2:29][C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 7010551N-alpha-t-Butyloxycarbonyl-S-(4-methyl-benzyl)-L-cysteineHCID 14330680Boc-Phe-betaAla-OH

Product 1

HCID 131717606Boc-Cys(MBzl)-Phe-betaAla-OH

Procedure

Using Boc-Phe-βAla-OH (prepared with 1.31 g Boc-Phe-βAla-OH.CHA), 1.02 g Boc-Cys(MBzl)-OH, 0.60 g HONB and 0.68 g DCC, the desired product was obtained in exactly the same manner as in Example 1-(XX), and was then crystallized with ether and collected by filtration.

Sources & evidence

ORD record
ord-6ddf0c2b6db74465a115e68024445991
Source dataset
uspto-grants-1992_10
Patent number
US05159061

Reaction notes

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