4-Nitrophenol → Z-Phe-ONp

HRID 1287253Notes

Reaction equation

HRID 1287253 reaction equation
[C:1]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[C:25](O)[CH:24]=1.C([N+]#[C-])(C)C>C(OCC)(=O)C>[N+:29]([C:28]1[CH:23]=[CH:24][C:25]([O:21][C:20](=[O:22])[C@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:11][C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])=[CH:26][CH:27]=1)([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 150783Isopropyl isocyanide

Product 1

HCID 151025Z-Phe-ONpYield 53.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6.0 g (20 mM) N-carbobenzoxy-L-phenylalanine, 3.3 g (24 mM) p-nitrophenol, and 1.6 g (24 mM) isopropyl isonitrile in 50 ml ethyl acetate was held at 60°C for 40 hours, and then evaporated. The residue was dissolved in ethanol, and the solution stored in a refrigerator until crystals formed. The crystals were filtered out, washed with petroleum ether, and dried. 4.5 g N-Carbobenzoxy-L-phenylalanine p-nitrophenyl ester was obtained (53% yield). M.P. 125.5° - 127°C. [α]D25 = -8.0° (C = 2.2, in chloroform).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethanol
  3. customformed
  4. filtrationThe crystals were filtered out
  5. washwashed with petroleum ether
  6. customdried

Sources & evidence

ORD record
ord-ecf5e5051d33488db183505b3dd04a96
Source dataset
uspto-grants-1976_10
Patent number
US03984417

Reaction notes

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