4-Nitrophenol → 58651-76-6

HRID 1440655Notes

Reaction equation

HRID 1440655 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][S:4][CH2:5][NH:6][C:7]([CH3:9])=[O:8].[CH:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[C:22](O)[CH:21]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([O:12][C:22]1[CH:21]=[CH:20][C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=1)=[O:11])[CH2:3][S:4][CH2:5][NH:6][C:7]([CH3:9])=[O:8]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 88223S-(acetamidomethyl)-N-(tert-butoxycarbonyl)-L-cysteine

Product 1

HCID 1293226358651-76-6Yield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

BocCys(Acm)ONp is prepared from BocCys(Acm)OH (Novabiochem, Laufelingen, CH) and p-nitrophenol by reaction with N,N'-dicyclohexylcarbodiimide (DCC) in etyl acetate and used without purification for the preparation of Boc-Cys(Acm)-Pro-OH (XII) by reacting it with H-Pro-OH in DMF/etyl acetate/H2O at 0° C. while keeping pH neutral by addition of Et3N. Yield 81%. Purity>95% (TLC).

Workup

  1. customused without purification for the preparation of Boc-Cys(Acm)-Pro-OH (XII)
  2. customat 0° C.
  3. additionwhile keeping pH neutral by addition of Et3N

Sources & evidence

ORD record
ord-88ec551267e14a9ab25c5e829cd4a6ba
Source dataset
uspto-grants-1996_03
Patent number
US05500413

Reaction notes

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