Phosphate → HCID 10571982, compound

HRID 1708521Notes

Reaction equation

HRID 1708521 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[N:11]2[C:12](=[O:24])[C@H:13]([C@H:14]([O:16][Si](C(C)(C)C)(C)C)[CH3:15])[C@H:10]2[C@@H:9]([CH3:25])[C:8]=1[S:26][C@H:27]1[CH2:31][NH:30][C:29](=[S:32])[CH2:28]1)=[O:6])[CH:2]=[CH2:3].F.[NH4+].P([O-])([O-])([O-])=O>CN(C)C=O>[CH2:1]([O:4][C:5]([C:7]1[N:11]2[C:12](=[O:24])[C@H:13]([C@H:14]([OH:16])[CH3:15])[C@H:10]2[C@@H:9]([CH3:25])[C:8]=1[S:26][C@H:27]1[CH2:31][NH:30][C:29](=[S:32])[CH2:28]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 10720094HCID 10720094, compoundHCID 13685747Ammonium hydrogenfluoride

Product 1

HCID 10571982HCID 10571982, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio ]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid allyl ester (1.00 g), dimethylformamide (10 ml) and ammonium hydrogenfluoride (459 mg) is stirred at room temperature for three days. To the reaction solution is added a phosphate buffer (pH 7.0), and the mixture is extracted with ethyl acetate. The organic layer is washed with a phosphate buffer, and the both of the phosphate buffer layers are combined, and extracted with ethyl acetate. The organic layers are combined, washed, dried and concentrated under reduced pressure. The resulting residue is crystallized from a mixture of ethyl acetate and n-hexane (2:1) to give (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid allyl ester (657 mg). The filtrate of the above crystallization is concentrated under reduced pressure, and the residue is purified by silica gel flash column chromatography (solvent; chloroform:ethanol=30:1), and further crystallized from a mixture of ethyl acetate and n-hexane (2:1) to give (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid allyl ester (24 mg).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with a phosphate buffer
  3. extractionextracted with ethyl acetate
  4. washwashed
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is crystallized from a mixture of ethyl acetate and n-hexane (2:1)

Sources & evidence

ORD record
ord-2df04b65ad8c4ea3902a3928d1115f90
Source dataset
uspto-grants-1994_10
Patent number
US05359059

Reaction notes

Loading…