Ethanol → (S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-nitrophenyl)propanoate

HRID 271316Notes

Reaction equation

HRID 271316 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.Cl.CN(C)[CH2:26][CH2:27]CN=C=NCC.C(O)C.CN(C1C=CC=CN=1)C>ClCCl>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([O:15][CH2:26][CH3:27])=[O:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Product 1

HCID 10593086(S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-nitrophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g of Boc-Phe(4-NO2)-OH, 3.09 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 5 ml of ethanol and 2 g of dimethylaminopyridine were stirred in dichloromethane for 3 days. The obtained substance was washed with 1N hydrochloric acid, an aqueous solution of saturated sodium hydrogen carbonate and saturated NaCl solution, and dried with magnesium sulfate. The solvent was removed to obtain the title compound.

Workup

  1. washThe obtained substance was washed with 1N hydrochloric acid
  2. dry with materialan aqueous solution of saturated sodium hydrogen carbonate and saturated NaCl solution, and dried with magnesium sulfate
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-15b45a522c8e48c7bbda57da8c517cf0
Source dataset
uspto-grants-2008_11
Patent number
US07452905B2

Reaction notes

Loading…