Isobutyl chloroformate → HCID 73944605, compound

HRID 2418570Notes

Reaction equation

HRID 2418570 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[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.[NH2:23][C@H:24]([C:34]([O:36][CH3:37])=[O:35])[CH2:25][CH2:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].Cl.ClC(OCC(C)C)=O>>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:23][C@H:24]([C:34]([O:36][CH3:37])=[O:35])[CH2:25][CH2:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[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 70878Benzyloxycarbonyl-L-phenylalanineHCID 16218751L-Glutamic acid, 5-(1,1-dimethylethyl) 1-methyl ester, hydrochloride (1:1)

Product 1

HCID 73944605HCID 73944605, compoundYield 88%

Procedure

Condensation of ZPheOH (3.00 g.) and HGlu(tBu)OMe hydrochloride salt (2.54 g.) by the mixed anhydride method using isobutyl chloroformate gave ZPhe-Glu(tBu)OMe in 88% yield. Debenzyloxycarbonylation of ZPhe-Glu(tBu)OMe (4.30 g.) by hydrogenation with palladium catalyst gave HPhe-Glu(tBu)OMe, which was not isolated but immediately condensed with BocPro-PheOH (3.12 g.) using dicyclohexylcarbodiimide and hydroxysuccinimide, affording BocPro-Phe-Phe-Glu(tBu)OMe in 22% yield. Hydrazinolysis of BocPro-Phe-Phe-Glu(tBu)OMe (1.09 g.) gave BocPro-Phe-Phe-Glu(tBu)NHNH2 in 58% yield.

Sources & evidence

ORD record
ord-a9b9db0a55fe4e48b740bcc8290e5421
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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