Isobutyl chloroformate → HCID 44576190, compound

HRID 236456Notes

Reaction equation

HRID 236456 reaction equation
[C:1]([NH:4][C@H:5]([C:13]([NH:15][CH2:16][C:17]([NH:19][C@H:20]([C:22]([OH:24])=O)[CH3:21])=[O:18])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].Cl.[Cl:26][CH2:27]C(CCl)=O.[NH2:32][C@H:33]([C:38]([OH:40])=O)[CH2:34][CH:35]([CH3:37])[CH3:36].ClC(OCC(C)C)=O>>[NH:4]([C:1]([CH3:2])=[O:3])[C@H:5]([C:13]([NH:15][CH2:16][C:17]([NH:19][C@H:20]([C:22]([NH:32][C@H:33]([C:38]([CH2:27][Cl:26])=[O:40])[CH2:34][CH:35]([CH3:36])[CH3:37])=[O:24])[CH3:21])=[O:18])=[O:14])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 62365Isobutyl chloroformateHCID 54438809HCID 54438809, compoundHCID 131715016HCID 131715016, compound

Product 1

HCID 44576190HCID 44576190, compound

Procedure

Ac-Phe-Gly-Ala-LeuCH2Cl was prepared by condensation of N-acetyl-L-phenylalanylglycyl-L-alanine with leucine chloromethyl ketone hydrochloride using a mixed anhydride procedure employing isobutyl chloroformate. Powers et al., Biochem. Biophys. Acta. 480:246-261 (1977), describe an analogous procedure. Crude product was recrystallized from ethyl acetate to provide a white crystalline solid, m.p. 152.4°-153.8° (reported m.p. 167°-168°).

Workup

  1. customCrude product was recrystallized from ethyl acetate
  2. customto provide a white crystalline solid, m.p. 152.4°-153.8° (reported m.p. 167°-168°)

Sources & evidence

ORD record
ord-907cd48f89a94508993b01b36dd1150d
Source dataset
uspto-grants-1987_02
Patent number
US04644055

Reaction notes

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