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

HRID 43595Notes

Reaction equation

HRID 43595 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:19][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][CH2:19][CH:4]([C:3]([O:2][CH3:1])=[O:21])[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 67548939N-(3-Methoxy-4-nitrobenzoyl)serine methyl ester

Product 1

HCID 68406207Methyl 2-(3-methoxy-4-nitrophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylateYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The same operation as in Example (97b) was performed using N-(3-methoxy-4-nitrobenzoyl)serine methyl ester obtained in Example (102a) (2.46 g, 8.26 mmol), the Burgess reagent (2.56 g, 10.7 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 1.72 g of the title compound as a light yellow solid (74%).

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-405438eb0a2445e59c18e530c061efde
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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