Acetyl chloride → HCID 13175939, compound

HRID 2413403Notes

Reaction equation

HRID 2413403 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[S:7][C:8]([C:11]2[CH2:18][S:17][CH:16]3[N:13]([C:14](=[O:27])[CH:15]3[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]=2[C:28]([O:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=[CH:9][N:10]=1.C(N(CC)CC)C>O1CCCC1>[C:1]([NH:5][C:6]1[S:7][C:8]([C:11]2[CH2:18][S:17][CH:16]3[N:13]([C:14](=[O:27])[CH:15]3[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]=2[C:28]([O:30][CH:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:29])=[CH:9][N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 131759453-(2-Aminothiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 13175939HCID 13175939, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of acetyl chloride (1.51 cc) in dry tetrahydrofuran (10 cc) is added dropwise, in 5 minutes, to a solution, cooled to 0° C., of 3-(2-aminothiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (10 g) in dry tetrahydrofuran (150 cc), and a solution of triethylamine (2.8 cc) in dry tetrahydrofuran (5 cc) is then added. The reaction mixture is stirred for 1 hour 30 minutes at about 0°-5° C. and is then treated with further acetyl chloride (1.51 cc) in tetrahydrofuran (10 cc). After 1 hour 50 minutes at 5° C., the reaction mixture is filtered and the filtrate is concentrated to 50 cc and diluted with ethyl acetate (250 cc). The organic phase is washed with a saturated sodium bicarbonate solution (100 cc), with distilled water (100 cc) and with a half-saturated sodium chloride solution (100 cc) and is then dried over magnesium sulphate and concentrated to dryness. Crude 3-(2-acetylamino-thiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicylo[4.2.0]oct-2-ene (10 g) is obtained in the form of a brown froth. Crystallisation from acetonitrile (25 cc) gives pure 3-(2-acetylamino-thiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (5.9 g) in the form of a whitish crystalline powder whose characteristics are identical to those of the product obtained in variant (A).

Workup

  1. waitAfter 1 hour 50 minutes at 5° C.
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated to 50 cc
  4. additiondiluted with ethyl acetate (250 cc)
  5. washThe organic phase is washed with a saturated sodium bicarbonate solution (100 cc), with distilled water (100 cc) and with a half-saturated sodium chloride solution (100 cc)
  6. dry with materialis then dried over magnesium sulphate
  7. concentrationconcentrated to dryness
  8. customCrude 3-(2-acetylamino-thiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicylo[4.2.0]oct-2-ene (10 g) is obtained in the form of a brown froth
  9. customCrystallisation from acetonitrile (25 cc)

Sources & evidence

ORD record
ord-7639c3e376d7446cbf5a6711900e5417
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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