Water → HCID 131716365, compound

HRID 1649849Notes

Reaction equation

HRID 1649849 reaction equation
C([O:4][C@H:5]([CH3:35])[C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][CH2:16]2)[N:13]=1)=[O:7])(=O)C.O.[OH-].[Na+]>CO>[C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([O:21][CH:22]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:19][CH2:20]2)[N:13]=1)(=[O:7])[C@@H:5]([CH3:35])[OH:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54124482HCID 54124482, compound

Product 1

HCID 131716365HCID 131716365, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cooled mixture of 2-((2R)-2-acetoxypropionylamino)-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (2.1 g), water (4 ml) and methanol (17 ml) was added dropwise 1N sodium hydroxide solution (3 ml). After the addition had been completed, the reaction mixture was kept at 5° C. for 1 hour and allowed to warm to ambient temperature. After standing overnight at the same temperature, the reaction mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (30:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was triturated with 70% ethanol to give white powder. Recrystallization from 70% ethanol gave 2-(D-lactoylamino)-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (1.13 g).

Workup

  1. additionAfter the addition
  2. waitAfter standing overnight at the same temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. washeluted with a mixture of chloroform and methanol (30:1 V/V)
  9. additionThe fractions containing the object compound
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was triturated with 70% ethanol
  12. customto give white powder
  13. customRecrystallization from 70% ethanol

Sources & evidence

ORD record
ord-82e31142c0d84e508ba53ebfc4d7b2bd
Source dataset
uspto-grants-1990_05
Patent number
US04921887

Reaction notes

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