Methyl valinate hydrochloride → Methyl 3-methyl-2-(5-(4-nitrophenyl)oxazole-2-carboxamido)butanoate

HRID 1024426Notes

Reaction equation

HRID 1024426 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15]([O:17]CC)=O)=[N:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH3:21][O:22][C:23](=[O:29])[C@H:24]([CH:26]([CH3:28])[CH3:27])[NH2:25]>CCN(CC)CC>[CH3:27][CH:26]([CH3:28])[CH:24]([NH:25][C:15]([C:13]1[O:14][C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[CH:11][N:12]=1)=[O:17])[C:23]([O:22][CH3:21])=[O:29]

Participants

4

Reactant 2

HCID 111190Methyl valinate hydrochlorideHCID 22350462Ethyl 5-(4-nitrophenyl)-1,3-oxazole-2-carboxylate

Product 1

HCID 67150348Methyl 3-methyl-2-(5-(4-nitrophenyl)oxazole-2-carboxamido)butanoateYield 31%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
110 °C

Procedure

An ethanolic solution of Ethyl 5-(4-nitrophenyl)oxazole-2-carboxylate (step D product, 3.4 g) and L-valine methyl ester hydrochloride (5.43 g) previously neutralized with Et3N (4.52 ml), was heated in a sealed tube at 110° C. for 2 days. EtOH was removed under reduced pressure and the crude material was chromatographed on silica gel in 1:9 EtOAc:Pet ether to get cream colored solid which was crystallized in EtOAc/pet ether to yield 700 mg (31%) of the title compound. 1HNMR (DMSO-d6, 300 MHz): δ 9.2 (d, 1H), 8.37 (d, 2H), 8.24 (s, 1H), 8.14 (d, 2H), 4.32 (m, 1H), 3.68 (s, 3H), 2.26 (m, 1H), 0.96 (t, 6H); MS (ES+): m/z 348 (M+1).

Workup

  1. customEtOH was removed under reduced pressure
  2. customthe crude material was chromatographed on silica gel in 1:9 EtOAc
  3. customPet ether to get cream colored solid which
  4. customwas crystallized in EtOAc/pet ether

Sources & evidence

ORD record
ord-107549a1ea3244269f8af3a1e0f26f91
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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