Methanol → HCID 131719094, compound

HRID 1757132Notes

Reaction equation

HRID 1757132 reaction equation
[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:2]([C:4]([NH:6][C@H:7]([C:9]([NH:11][C@H:12]([C:15]([OH:17])=O)[CH2:13][CH3:14])=[O:10])[CH3:8])=[O:5])[CH3:3].[CH2:28]([O:35][CH2:36]C1C=CC=CC=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Na].C(Cl)(Cl)Cl.C[OH:49]>C(O)C1C=CC=CC=1.O>[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:2]([C:4]([NH:6][C@H:7]([C:9]([NH:11][CH:12]([C:15]([C:36]([O:35][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:49])=[O:17])[CH2:13][CH3:14])=[O:10])[CH3:8])=[O:5])[CH3:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 66729449CID 66729449HCID 131719095Z-Ala-Ala-Abu-OH

Product 1

HCID 131719094HCID 131719094, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 962WaterSolvent

Procedure

This compound was prepared from Z-Ala-Ala-Abu-OH in 31% yield by the procedure described in Example PKC1, except that benzyl oxalyl chloride was used in the Dakin-West reaction and sodium benzyloxide in benzyl alcohol was used for enol ester hydrolysis; single spot on tlc, Rf2 =0.40 (CHCl3 :MeOH=9:1); mp 124°-125° C.; MS, m/e=498 (M+ +1). Anal. Calcd. for C26H31O7N3.2/3 H2O: C, 61.28; H, 6.39; N, 8.24. Found: C, 61.14; H, 6.65; N, 7.94.

Sources & evidence

ORD record
ord-7d4915603a1e4b618a03bc27a3d00dfd
Source dataset
uspto-grants-1995_08
Patent number
US05444042

Reaction notes

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