Benzyl Bromide → HCID 20201320, compound

HRID 979020Notes

Reaction equation

HRID 979020 reaction equation
C(OC([NH:8][CH:9]([CH:13]([CH3:16])[CH:14]=[CH2:15])[C:10]([OH:12])=[O:11])=O)(C)(C)C.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C(O)=O>[NH2:8][CH:9]([CH:13]([CH3:16])[CH:14]=[CH2:15])[C:10]([O:12][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:11]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 12839939HCID 12839939, compound

Product 1

HCID 20201320HCID 20201320, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The substrate tripeptide A used in the process, δ-(L-α-aminoadipoyl)-L-cysteinyl-D-γ,δ-didehydroisoleucine, is prepared in the following manner. First, 2-(t-butyloxycarbonylamino)-3-methylpent-4-eneoic acid (prepared according to the method of P. A. Bartlett and J. F. Barstow, J. Org. Chem., 1982, 47, 3933) is esterified with benzyl bromide and sodium bicarbonate. The benzyl ester is treated with formic acid to remove the t-BOC amino-protecting group to provide the amino ester, benzyl 2-amino-3-methylpent-4-eneoate, as the formate salt as shown below. ##STR3##

Workup

  1. customis prepared in the following manner
  2. customto remove the t-BOC amino-

Sources & evidence

ORD record
ord-2cf56eb1187243a4a1e6a2ca26aaa300
Source dataset
uspto-grants-1987_05
Patent number
US04666835

Reaction notes

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