Acetyl chloride → HCID 86753798, compound

HRID 1417605Notes

Reaction equation

HRID 1417605 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[CH2:21][C@:20]3([CH3:34])[C@@H:22]([CH3:33])[CH2:23][CH2:24][C@H:25]4[C:26]([CH3:32])([CH3:31])[C@@H:27]([OH:30])[CH2:28][CH2:29][C@@:19]34[O:18][C:11]=2[C:12]2[CH2:13][NH:14][CH2:15][C:16]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:41](Cl)(=[O:43])[CH3:42]>C(Cl)(Cl)Cl>[C:41]([N:14]1[CH2:13][C:12]2[C:11]3[O:18][C@@:19]45[CH2:29][CH2:28][C@H:27]([OH:30])[C:26]([CH3:32])([CH3:31])[C@@H:25]4[CH2:24][CH2:23][C@H:22]([CH3:33])[C@@:20]5([CH3:34])[CH2:21][C:10]=3[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][C:16]=2[CH2:15]1)(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10340Sodium Carbonate2×HCID 86753797HCID 86753797, compound

Product 1

HCID 86753798HCID 86753798, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of Compound (33a) (47 mg, 0.10 mmol) in 5.0 ml of chloroform was added a sodium carbonate aqueous solution (prepared from 14 mg (0.10 mmol) of sodium carbonate and 5.0 ml of water). Under ice-cooling, to the mixture was added 8 μl (0.12 mmol) of acetyl chloride dissolved in 0.3 ml of chloroform in a single portion with vigorous stirring. After the reaction mixture was stirred for 30 min and warmed up to room temperature, it was extracted with chloroform. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by a column chromatography (Merck, Lobar column, size A; ethyl acetate) to give 47 mg (92%) of Compound (33b).

Workup

  1. temperatureUnder ice-cooling, to the mixture
  2. extractionit was extracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a column chromatography (Merck, Lobar column, size A

Sources & evidence

ORD record
ord-b55e4f18c1a344749680f2f8d91b298a
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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