4-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester → HCID 11589947, compound

HRID 1695265Notes

Reaction equation

HRID 1695265 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:31])[C:8]2[O:14][C:13]3[C:15]([Cl:27])=[CH:16][C:17]([NH:19][C:20](=[O:26])[CH2:21][O:22][C:23](=[O:25])[CH3:24])=[CH:18][C:12]=3[CH2:11][S:10](=[O:29])(=[O:28])[C:9]=2[CH:30]=1)=[O:4].COC(C1C=C(C)C2OC3C(Cl)=CC(NC(=O)CCl)=CC=3CS(=O)(=O)C=2C=1)=O>O.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:31])[C:8]2[O:14][C:13]3[C:15]([Cl:27])=[CH:16][C:17]([NH:19][C:20](=[O:26])[CH2:21][O:22][C:23](=[O:25])[CH3:24])=[CH:18][C:12]=3[CH2:11][S:10](=[O:29])(=[O:28])[C:9]=2[CH:30]=1)=[O:4].[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:31])[C:8]2[O:14][C:13]3[C:15]([Cl:27])=[CH:16][C:17]([NH:19][C:20](=[O:26])[CH2:21][OH:22])=[CH:18][C:12]=3[CH2:11][S:10](=[O:29])(=[O:28])[C:9]=2[CH:30]=1)=[O:4]

Participants

6

Reactant 2

HCID 116336414-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl esterHCID 11669941HCID 11669941, compound

Product 2

HCID 11589947HCID 11589947, compoundYield 2%HCID 11669941HCID 11669941, compoundYield 1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-(2-Acetoxy-acetylamino)-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester (B) Sodium acetate (0.054 g, 0.658 mmol) in water (5 mL) was added to solution of compound of Example 4 (0.18 g, 0.405 mmol) in DMF (5 mL) at 25° C. and then the reaction mixture was stirred at 80° C. for 6 h. The solvent was removed under vacuum, water (15 mL) was added and extracted using ethyl acetate (3×30 mL). Combined organic layer was washed with water (2×100 mL), brine (100 mL) and dried over anhydrous sodium sulfate. The solvent was removed under vacuum and crude product was purified by column chromatography (silica gel) to obtain the title compound (B) (1% methanol in chloroform) and compound (A) (2% methanol in chloroform).

Workup

  1. customThe solvent was removed under vacuum, water (15 mL)
  2. additionwas added
  3. extractionextracted
  4. washCombined organic layer was washed with water (2×100 mL), brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under vacuum and crude product
  7. customwas purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-c9181241a5334e118e4fd57842d51090
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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