Acetyl chloride → HCID 12085344, compound

HRID 896446Notes

Reaction equation

HRID 896446 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[O:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C@@H:10]1[CH2:19][N:20]([CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[C:39](=[O:40])[C:38]2[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=2[S:36]1(=[O:46])=[O:45])[C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCCl>[C:5]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[O:9][C@@H:10]([CH2:19][N:20]([CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[C:39](=[O:40])[C:38]3[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=3[S:36]1(=[O:46])=[O:45])[C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:11][CH2:12]2)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12085343HCID 12085343, compound

Product 1

HCID 12085344HCID 12085344, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

12.7 g (95 mmol) of anhydrous aluminum chloride are suspended in 10 ml of 1,2-dichloroethane. At 0° C., initially 5.9 ml (82 mmol) of acetyl chloride are added. At 0° C., a solution of 34 g (63 mmol) of benzyl (2R)-3,4-dihydro-2H-chromen-2-ylmethyl[4-(1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)butyl]carbamate in 100 ml of 1,2-dichloroethane is slowly added dropwise to this mixture. The reaction is stirred at room temperature overnight. The mixture is poured into ice-water and the organic phase is then separated off and the aqueous phase is repeatedly extracted with dichloromethane. The combined organic extracts are dried over magnesium sulfate and concentrated. The resulting crude product is purified by chromatography (silica gel, mobile phase toluene/ethyl acetate 3:1). This gives 9.6 g (26.5% of theory) of benzyl [(2R)-6-acetyl-3,4-dihydro-2H-chromen-2-yl]methyl[4-(1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)butyl]carbamate.

Workup

  1. customthe organic phase is then separated off
  2. extractionthe aqueous phase is repeatedly extracted with dichloromethane
  3. dry with materialThe combined organic extracts are dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude product is purified by chromatography (silica gel, mobile phase toluene/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-8d08a42f6ee246c2b15cf4465816e5c9
Source dataset
uspto-grants-2005_07
Patent number
US06919360B2

Reaction notes

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