Chloroacetyl chloride → HCID 22857202, compound

HRID 129236Notes

Reaction equation

HRID 129236 reaction equation
[CH3:1][C@@:2]12[C:11]3[C:12]([S:18]([C:21]4[C:26]([CH:27]([CH3:29])[CH3:28])=[CH:25][C:24]([CH:30]([CH3:32])[CH3:31])=[CH:23][C:22]=4[CH:33]([CH3:35])[CH3:34])(=[O:20])=[O:19])=[CH:13][CH:14]=[C:15]4[NH:16][CH:17]=[C:9]([C:10]=34)[CH2:8][C@H:3]1[NH:4][CH2:5][CH2:6][O:7]2.C(=O)([O-])[O-].[Na+].[Na+].[Cl:42][CH2:43][C:44](Cl)=[O:45]>C(OCC)(=O)C>[Cl:42][CH2:43][C:44]([N:4]1[C@@H:3]2[CH2:8][C:9]3[C:10]4[C:15]([NH:16][CH:17]=3)=[CH:14][CH:13]=[C:12]([S:18]([C:21]3[C:22]([CH:33]([CH3:35])[CH3:34])=[CH:23][C:24]([CH:30]([CH3:32])[CH3:31])=[CH:25][C:26]=3[CH:27]([CH3:29])[CH3:28])(=[O:20])=[O:19])[C:11]=4[C@@:2]2([CH3:1])[O:7][CH2:6][CH2:5]1)=[O:45]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 22857197HCID 22857197, compound

Product 1

HCID 22857202HCID 22857202, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-4,6,6a,8,9,10a-hexahydro-10a-methyl-1-(2,4,6-triisopropylphenylsulfonyl)-7H-indolo[3,4-gh][1.4]benzoxazine (106 mg, 0.21 mmol) in ethyl acetate (10 ml) was added a saturated aqueous solution of sodium carbonate (2 ml). To the mixture was added, while stirring vigorously, chloroacetyl chloride (1.2 equivalent). After completion of the reaction, the organic layer was separated, washed with an aqueous saline solution and dried (anhydrous Na2SO4). The solvent was distilled off under reduced pressure, and the residue was subjected to a silica gel column chromatography, eluting with n-hexane-ethyl acetate (4:1) to afford 109 mg (89%) of the title compound as an amorphous crystalline product.

Workup

  1. additionTo the mixture was added
  2. customAfter completion of the reaction
  3. customthe organic layer was separated
  4. washwashed with an aqueous saline solution
  5. dry with materialdried (anhydrous Na2SO4)
  6. distillationThe solvent was distilled off under reduced pressure
  7. washeluting with n-hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-796927a874824f6598cb24ade9c0f3bd
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

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