Methanol → HCID 19603813, compound

HRID 1604688Notes

Reaction equation

HRID 1604688 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21](=[O:42])[CH2:22][N:23]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:25]([C:32]([O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[O:33])=[CH:24]4)=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)([CH3:6])([CH3:5])[CH3:4].CO.O1CCCC1>C([O-])(=O)C.[NH4+]>[C:3]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([CH:21]([OH:42])[CH2:22][N:23]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:25]([C:32]([O:34][CH2:35][C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)=[O:33])=[CH:24]4)=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 19603768HCID 19603768, compound

Product 1

HCID 19603813HCID 19603813, compound

Reagents, catalysts & solvents 1

HCID 517165Ammonium AcetateSolvent

Procedure

Sodium borohydride (4 mg) was added to a solution of benzyl 1-{2-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-2-oxoethyl}indole-3-carboxylate in a mixed solvent of methanol (1 ml) and tetrahydrofurane (5 ml). After being stirred for several hours, the reaction mixture was diluted with aqueous ammonium acetate solution, which was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give benzyl 1-{2-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-2-hydroxyethyl}indole-3-carboxylate (70 mg).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with a mixture of toluene and ethyl acetate
  6. additionThe fractions containing the objective compound
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd303f697b394a49aaa924874353302b
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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