Potassium hydride → HCID 23678574, compound

HRID 1584406Notes

Reaction equation

HRID 1584406 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[K+:16]>CN(C)C=O>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S-:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+:16]

Participants

4

Reactant 2

HCID 82127Potassium hydrideHCID 27603544-Phenoxythiophenol

Product 1

HCID 23678574HCID 23678574, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Phenoxythiophenol (4.8 g) was stirred for 45 min with potassium hydride (0.98 g) in N,N-dimethylformamide (100 ml) to produce a homogeneous solution of potassium 4-phenoxythiophenolate. The lactone, (S)-3-carbobenzyl-oxyamino-2-oxetanone (5.3 g) (Arnold, L. D. et al., J. Am. Chem. Soc., 107, 7105 (1985)), dissolved in N,N-dimethylformamide (50 ml) was then added at room temperature. After stirring for 30 minutes the mixture was poured into water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate, and solvent removed under reduced pressure to give (R)-2-(benzyloxycarbonylamino)-3-(4-phenoxyphenylthio)-propionic acid (9.2 g). It can be used directly in the next step.

Sources & evidence

ORD record
ord-50394cfebe06429fb6036bb6dbfa0b6b
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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