Dicyclohexylcarbodiimide → BocGly-Leu-MetNH2

HRID 2418549Notes

Reaction equation

HRID 2418549 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.[NH2:13][C@H:14]([C:20]([NH:22][C@H:23]([C:28]([NH2:30])=[O:29])[CH2:24][CH2:25][S:26][CH3:27])=[O:21])[CH2:15][CH2:16][CH:17](C)C.Cl.[CH:32]1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([NH:13][C@H:14]([C:20]([NH:22][C@H:23]([C:28]([NH2:30])=[O:29])[CH2:24][CH2:25][S:26][CH3:27])=[O:21])[CH2:15][CH:16]([CH3:17])[CH3:32])=[O:5]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 80170N-HydroxysuccinimideHCID 131713703HLeu-MetNH2 hydrochloride

Product 1

HCID 15602549BocGly-Leu-MetNH2Yield 51%

Procedure

Condensation of BocGlyOH (4.4 g.) and HLeu-MetNH2 hydrochloride salt (Example 1, 7.5 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocGly-Leu-MetNH2 in 51% yield. De-t-butoxycarbonylation of BocGly-Leu-MetNH2 using hydrogen chloride in acetic acid gave HGly-Leu-MetNH2 hydrochloride salt in 56% yield.

Sources & evidence

ORD record
ord-1737be434aca4612a0c1ebd69348a7fd
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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