Isobutyl chloroformate → BocDPhe-Leu-MetNH2

HRID 2418585Notes

Reaction equation

HRID 2418585 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:20][C@H:21]([C:27]([NH:29][C@H:30]([C:35]([NH2:37])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:22][CH2:23][CH:24](C)C.Cl.Cl[C:40](OCC(C)C)=O>>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([NH:20][C@H:21]([C:27]([NH:29][C@H:30]([C:35]([NH2:37])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:22][CH:23]([CH3:24])[CH3:40])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 62365Isobutyl chloroformateHCID 637610Boc-D-phenylalanineHCID 131713703HLeu-MetNH2 hydrochloride

Product 1

HCID 131713767BocDPhe-Leu-MetNH2Yield 57%

Procedure

Condensation of BocDPheOH (2.65 g.) and HLeu-MetNH2 hydrochloride salt (Example 1, 2.98 g.) by the mixed anhydride method using isobutyl chloroformate gave BocDPhe-Leu-MetNH2 in 57% yield. De-t-butoxycarbonylation of BocDPhe-Leu-MetNH2 (2.7 g.) using hydrogen chloride in ethyl acetate gave HDPhe-Leu-MetNH2 hydrochloride salt in 82% yield.

Sources & evidence

ORD record
ord-a05df0a55dc341ffa694100e0771641d
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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