Z-Phe-Gly-Leu-OH → Z-Phe-Gly-Leu-LeuCH3

HRID 236469Notes

Reaction equation

[NH:1]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22](O)=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:35][C@H:36]([C:41]([CH3:43])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39].Br.N(C(OCC1C=CC=CC=1)=O)[C@H](C(NCC(N[C@H](C(N[C@H](C(C)=O)CC(C)C)=O)C)=O)=O)CC1C=CC=CC=1>>[NH:1]([C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([NH:35][C@H:36]([C:41]([CH3:43])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:23])[CH2:18][CH:19]([CH3:20])[CH3:21])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Reactant 3

HCID 131715018Z-Phe-Gly-Leu-OH

HCID 131715061H-LeuCH3.HBr

HCID 131715062Z-Phe-Gly-Ala-LeuCH3

Product 1

HCID 131715060Z-Phe-Gly-Leu-LeuCH3

Procedure

Z-Phe-Gly-Leu-LeuCH3 was prepared by coupling Z-Phe-Gly-Leu-OH (2.23 g. 4.76 mmol) to H-LeuCH3.HBr by a procedure substantially similar to that described for preparation of Z-Phe-Gly-Ala-LeuCH3, above. Product was recrystallized from ethyl acetate to yield 2.34 g of Z-Phe-Gly-Leu-LeuCH3 (m.p. 165.5°-166.5°).

Workup

customZ-Phe-Gly-Leu-LeuCH3 was prepared
customProduct was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-42f958fab50347ab8b17797dba67a336
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04644055

Reaction notes

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