Water → HCID 14674510, compound

HRID 330478Notes

Reaction equation

HRID 330478 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:14][C:13]=3[CH:25]=2)[S:3]1.[BH4-].[Na+].O>CO.O1CCCC1>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH:17]([OH:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:14][C:13]=3[CH:25]=2)[S:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10545929HCID 10545929, compound

Product 1

HCID 14674510HCID 14674510, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.3 g of 5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-(benzoyl)benzoxazole are dissolved in a mixture of 30 ml of methanol and 6 ml of tetrahydrofuran, and 0.14 g of sodium borohydride is added thereto. After the mixture is stirred at room temerature for 5 minutes, water is added thereto. The solution is extracted with ethyl acetate, and the extract is evaporated to remove the solvent. The residue is crystallized with ether, whereby 0.64 g of 5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-(α-hydroxybenzyl)benzoxazole is obtained as colorless crystal.

Workup

  1. additionis added
  2. extractionThe solution is extracted with ethyl acetate
  3. customthe extract is evaporated
  4. customto remove the solvent
  5. customThe residue is crystallized with ether

Sources & evidence

ORD record
ord-9be6ab2f88ab4a3082d8f42f98b41723
Source dataset
uspto-grants-1990_01
Patent number
US04897393

Reaction notes

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