Acetyl chloride → HCID 13175949, compound

HRID 2413437Notes

Reaction equation

HRID 2413437 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[S:7][C:8]([C:11]2[CH2:18][O:17][CH:16]3[N:13]([C:14](=[O:39])[CH:15]3[NH:19][C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]=2[C:40]([O:42][CH:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])=[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][O:17][CH:16]3[N:13]([C:14](=[O:39])[CH:15]3[NH:19][C:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:12]=2[C:40]([O:42][CH:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[O:41])=[CH:9][N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13175943HCID 13175943, compound

Product 1

HCID 13175949HCID 13175949, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of acetyl chloride (0.11g) in dry tetrahydrofuran (2 cc) is added, in 3 minutes, to a solution, cooled to 0° C., of 3-(2-amino-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-7-tritylamino-5-oxa-1-azabicyclo[4.2.0]oct-2-ene (0.80 g) in dry tetrahydrofuran (10 cc), and a solution of triethylamine (0.18 cc) in dry tetrahydrofuran (2 cc) is then added. The mixture is stirred for 30 minutes at 0° C. and is then filtered over a diatomaceous earth powder. The filtrate is diluted with ethyl acetate (50 cc) and washed with distilled water (50 cc), a half-saturated sodium bicarbonate solution (50 cc) and a saturated sodium chloride solution (50 cc). The organic phase is dried over anhydrous sodium sulphate; it is filtered, the insoluble matter is washed with ethyl acetate (10 cc) and the organic solution is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue (0.89 g) is chromatographed on a column (height: 24 cm; diameter: 2.2 cm) of silica (0.04-0.06 mm), elution being carried out with a 40:60 (by volume) mixture of cyclohexane and ethyl acetate under 0.4 kPa, and 60 cc fractions being collected. Fractions 5 to 11 are combined and the solvent is evaporated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 3-(2-Acetylamino-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-7-tritylamino-5-oxa-1-azabicyclo[4.2.0]oct-2-ene (0.55 g) is obtained in the form of a pale chestnut-coloured froth.

Workup

  1. filtrationis then filtered over a diatomaceous earth powder
  2. additionThe filtrate is diluted with ethyl acetate (50 cc)
  3. washwashed with distilled water (50 cc)
  4. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  5. filtrationit is filtered
  6. washthe insoluble matter is washed with ethyl acetate (10 cc)
  7. concentrationthe organic solution is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  8. customThe residue (0.89 g) is chromatographed on a column (height: 24 cm; diameter: 2.2 cm) of silica (0.04-0.06 mm), elution
  9. additionbeing carried out with a 40:60 (by volume) mixture of cyclohexane and ethyl acetate under 0.4 kPa, and 60 cc fractions
  10. custombeing collected
  11. customthe solvent is evaporated under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-d08eec45d30945bb9d4a8124155642e2
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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