Acetic Anhydride → HCID 10861536, compound

HRID 2108189Notes

Reaction equation

HRID 2108189 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[C:8]1([CH:14]2[N:18]3[C:19](=[O:30])[N:20]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)C(O)[C@@H]3[CH2:16][S:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:8]1([CH:14]2[N:18]3[C:19](=[O:30])[N:20]([CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:5]([O:4][C:1](=[O:3])[CH3:2])[C@@H:6]3[CH2:16][S:15]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 15612061HCID 15612061, compound

Product 1

HCID 10861536HCID 10861536, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

33.69 g (0.33 mol) of acetic anhydride and 366.5 mg (3 mmol) of 4-(dimethylamino)-pyridine are added to a solution of 97.92 g (0.3 mol) of (7RS,7aR)-3-phenyl-6-benzyl-7,7a-dihydro-7-hydroxy-1H,3H-imidazo[1,5-c]-thiazol-5(6H)-one in 900 ml of toluene, and the solution is stirred for 2 hours at 40° C. After cooling to room temperature the solution is washed with 180 ml of water, with 180 ml of a saturated sodium bicarbonate solution and the solvent is distilled off. 109.8 g of (7RS,7aR)-3-phenyl-6-benzyl-7,7a-dihydro-7-acetoxy-1H,3H-imidazo[1,5-c]thiazol-5(6H)-one are obtained as an oil.

Workup

  1. temperatureAfter cooling to room temperature the solution
  2. washis washed with 180 ml of water, with 180 ml of a saturated sodium bicarbonate solution
  3. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-3b6cfbb74fb24f1a90ca9e8fdf7af4fa
Source dataset
uspto-grants-1990_06
Patent number
US04937351

Reaction notes

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