Sodium borohydride → 2-[3-(Hydroxy-o-tolyl-methyl)-4-methoxy-benzoylamino]-indane-2-carboxylic acid

HRID 2405272Notes

Reaction equation

HRID 2405272 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([NH:9][C:10]2([C:19]([OH:21])=[O:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)=[O:8])=[CH:5][C:4]=1[C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31].[BH4-].[Na+]>CO.C(O)C>[OH:32][CH:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])[C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][C:3]=1[O:2][CH3:1])[C:7]([NH:9][C:10]1([C:19]([OH:21])=[O:20])[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)=[O:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 670764642-[4-Methoxy-3-(2-methyl-benzoyl)-benzoylamino]-indane-2-carboxylic acid

Product 1

HCID 670765032-[3-(Hydroxy-o-tolyl-methyl)-4-methoxy-benzoylamino]-indane-2-carboxylic acidYield 18.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

The compound of example 240 (70 mg, 0.163 mmol) was dissolved in a mixture of methanol (1.5 ml) and ethanol (1.5 ml) and cooled in an ice bath. Sodium borohydride (18.9 mg, 0.49 mmol) was added in two batches and the mixture reacted with ice cooling until completion (3 h). The volatiles were evaporated and the residue was partitioned between diethyl ether and 1 N hydrochloric acid. The aqueous phase was extracted with diethyl ether, and the combined organic phases were dried and evaporated. The residue was purified by RP HPLC (water/ACN gradient) to yield 13 mg of the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. customthe mixture reacted with ice cooling until completion (3 h)
  3. customThe volatiles were evaporated
  4. customthe residue was partitioned between diethyl ether and 1 N hydrochloric acid
  5. extractionThe aqueous phase was extracted with diethyl ether
  6. customthe combined organic phases were dried
  7. customevaporated
  8. customThe residue was purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-9fd92a87370747c1a2042746b7405c01
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

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