N-Benzyloxycarbonyl-beta-alanine → HCID 19024519, compound

HRID 1033859Notes

Reaction equation

HRID 1033859 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([CH2:19][C:20]([O:22][CH3:23])=[O:21])#[C-:18].C(P(C#N)(CC)=O)C.N12CCCN=C1CCCCC2>CN(C)C=O.C(N(CC)CC)C>[CH3:23][O:22][C:20]([C:19]1[N:17]=[CH:18][O:16][C:14]=1[CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:21]

Participants

7

Reactant 4

HCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 547815Methyl isocyanoacetateHCID 13586794Diethylphosphorylcyanide

Product 1

HCID 19024519HCID 19024519, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 33.5 g of N-benzyloxycarbonyl-β-alanine, 15 g of methyl isocyanoacetate, 31.8 g of diethylphosphorylcyanide, 23 g of 1,8-diazabicyclo[5.4.0]undec-7-ene, 42 ml of triethylamine and 300 ml of dimethylformamide was stirred at room temperature overnight. Then, the solvent was removed, and ethyl acetate was added to the mixture. The mixture was washed and dried, and then the solvent was removed. The residue was purified by silica gel chromatography and crystallized from isopropyl ether, followed by recrystallization from an ethyl acetate-isopropyl ether mixed solution, to obtain 22.6 g of 4-methoxycarbonyl-5-{2-(benzyloxycarbonylamino)ethyl}oxazole.

Workup

  1. customThen, the solvent was removed
  2. additionethyl acetate was added to the mixture
  3. washThe mixture was washed
  4. customdried
  5. customthe solvent was removed
  6. customThe residue was purified by silica gel chromatography
  7. customcrystallized from isopropyl ether
  8. customfollowed by recrystallization from an ethyl acetate-isopropyl ether mixed solution

Sources & evidence

ORD record
ord-816e524574f54a1699579bb1ef63b781
Source dataset
uspto-grants-1994_05
Patent number
US05312826

Reaction notes

Loading…