Methyl N-(triethylammoniosulfonyl)carbamate → Methyl 2-(3-methoxy-4-nitrophenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate

HRID 43610Notes

Reaction equation

HRID 43610 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@H:4]([C@@H:19]([CH3:21])[OH:20])[NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([O:16][CH3:17])[CH:8]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:17][O:16][C:9]1[CH:8]=[C:7]([C:6]2[O:20][CH:19]([CH3:21])[CH:4]([C:3]([O:2][CH3:1])=[O:22])[N:5]=2)[CH:12]=[CH:11][C:10]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 67549208N-(3-Methoxy-4-nitrobenzoyl)threonine methyl ester

Product 1

HCID 67548884Methyl 2-(3-methoxy-4-nitrophenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The same operation as in Example (97b) was performed using N-(3-methoxy-4-nitrobenzoyl)threonine methyl ester obtained in Example (105a) (4.49 g, 14.4 mmol), the Burgess reagent (3.94 g, 16.5 mmol) and THF (50 mL). Purification by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 1/2) gave 3.6 g of the title compound as a light yellow solid (85%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 1/2)

Sources & evidence

ORD record
ord-6bb0929b14a246a49caa63642a84077d
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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