Methyl N-(triethylammoniosulfonyl)carbamate → Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate

HRID 43625Notes

Reaction equation

HRID 43625 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@H:4]([C@@H:26]([CH3:28])O)[NH:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[C:9]([CH3:24])[CH:8]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH2:17]([O:16][C:14]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[O:25][CH:26]([CH3:28])[CH:4]([C:3]([O:2][CH3:1])=[O:29])[N:5]=2)=[CH:8][C:9]=1[CH3:24])=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 68406078N-(4-{[(Benzyloxy)carbonyl]amino}-3-methylbenzoyl)threonine methyl ester

Product 1

HCID 67548562Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylateYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The same operation as in Example (97b) was performed using N-(4-{[(benzyloxy)carbonyl]amino}-3-methylbenzoyl)threonine methyl ester obtained in Example (108b) (5.37 g, 13.4 mmol), the Burgess reagent (4.0 g, 16.8 mmol) and THF (50 mL). Purification by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/3, 2/3, 3/2, 3/1) gave 4.42 g of the title compound as a colorless solid (86%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/3, 2/3, 3/2, 3/1)

Sources & evidence

ORD record
ord-8931ace2eca04ecfb43d7be9d73e4202
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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