Methanol → HCID 13754452, compound

HRID 2118845Notes

Reaction equation

HRID 2118845 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:20]1([OH:25])[CH2:24][CH2:23][S:22][CH2:21]1)[C:10]([O:12]CC1C=CC=CC=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[K+].CO>O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:20]1([OH:25])[CH2:24][CH2:23][S:22][CH2:21]1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 516893Potassium BicarbonateHCID 13754451HCID 13754451, compound

Product 1

HCID 13754452HCID 13754452, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A slurry of N-(t-butoxycarbonyl)-α-(3-hydroxy-2,3,4,5-tetrahydro-3-thiofuranyl)glycine, benzyl ester (2.65 g, 7.22 mmole) in 20 ml of water was treated with potassium bicarbonate (1.0 g, 7.8 mmole) followed by 15 ml of methanol. Stirring at 25° C. for 14 hours gave a homogeneous solution which was diluted with water and extracted with ethyl acetate. The aqueous layer was acidified with 10% potassium bisulfate, saturated with sodium chloride, and extracted with ethyl acetate. Drying (sodium sulfate) and evaporation of the organic layer, and trituration of the residue with isopropyl ether gave the product as a white solid, 1.25 g, melting point 116°-118° C.

Workup

  1. customgave a homogeneous solution which
  2. extractionextracted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. customDrying
  5. custom(sodium sulfate) and evaporation of the organic layer, and trituration of the residue with isopropyl ether

Sources & evidence

ORD record
ord-c74245f133ac4eb9b03d7623b384c047
Source dataset
uspto-grants-1987_07
Patent number
US04680388

Reaction notes

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