Water → HCID 68548837, compound

HRID 2243479Notes

Reaction equation

HRID 2243479 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:31][C:23]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[S:30][C:22]=2[C:21]=1[OH:32])=[O:19].O>CN(C=O)C>[CH3:16][O:17][C:18]([C:20]1[S:31][C:23]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[S:30][C:22]=2[C:21]=1[O:32][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 68540610HCID 68540610, compound

Product 1

HCID 68548837HCID 68548837, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl bromoacetate (0.082 ml, 0.56 mmol, 1.3 equiv) was added to a mixture of NaOt-Bu (50 mg, 1.2 equiv) and 1-hydroxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester (113 mg, 0.43 mmol, 1 equiv) in DMF (10 ml). The resulting mixture was stirred at 60° C. for 16 hr. Addition of water followed by extraction with EtOAc and washing with water left crude product. Purification by column chromatography gave 140 mg (86%) of 1-tert-butoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester as an orange solid.

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washwashing with water
  3. waitleft crude product
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-0f86bcc9bdf74aec8c75936ab88d0362
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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