Water → HCID 68542571, compound

HRID 2243481Notes

Reaction equation

HRID 2243481 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].CC([O-])(C)C.[Na+].[CH3:16][O:17][C:18]([C:20]1[S:32][C:23]2[C:24]3[CH:25]=[CH:26][C:27]([Cl:31])=[CH:28][C:29]=3[S:30][C:22]=2[C:21]=1[OH:33])=[O:19].O>CN(C=O)C>[CH3:16][O:17][C:18]([C:20]1[S:32][C:23]2[C:24]3[CH:25]=[CH:26][C:27]([Cl:31])=[CH:28][C:29]=3[S:30][C:22]=2[C:21]=1[O:33][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 79177tert-Butyl bromoacetateHCID 23676156Sodium t-butoxideHCID 68547479HCID 68547479, compound

Product 1

HCID 68542571HCID 68542571, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl bromoacetate (0.10 ml, 0.65 mmol, 1.3 equiv) was added to a mixture of NaOt-Bu (60 mg, 1.2 equiv) and 6-chloro-1-hydroxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester (150 mg, 0.5 mmol) in DMF (6 ml) and stirred at 60° C. for 2.5 hr then at RT for 3 days. Water was added and the mixture was extracted with EtOAc. After removal of solvent, purification by column chromatography gave 140 mg (68%) of 1-tert-butoxycarbonylmethoxy-6-chloro-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester as orange solids.

Workup

  1. waitat RT for 3 days
  2. extractionthe mixture was extracted with EtOAc
  3. customAfter removal of solvent, purification by column chromatography

Sources & evidence

ORD record
ord-a222ccb81d174a98bf589306778aa38a
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

Loading…