Acetic Acid → O-[3(R)-acetoxy-2-diazo-1-oxobutyl]-N-trifluoroacetyl-L-serine

HRID 2165243Notes

Reaction equation

HRID 2165243 reaction equation
[C:1]([O:4][C@H:5]([CH3:23])[C@H:6]([NH2:22])[C:7]([O:9][CH2:10][C@@H:11]([C:19]([OH:21])=[O:20])[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[O:8])(=[O:3])[CH3:2].ClCC(O)=O.[N:29]([O-])=O.[Na+].C(O)(=O)C>O>[C:1]([O:4][C@H:5]([CH3:23])[C:6](=[N+:22]=[N-:29])[C:7]([O:9][CH2:10][C@@H:11]([C:19]([OH:21])=[O:20])[NH:12][C:13](=[O:18])[C:14]([F:15])([F:17])[F:16])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 300Chloroacetic AcidHCID 18640000O-[3(R)-acetoxy-2(S)-amino-1-oxobutyl]-N-trifluoroacetyl-L-serineHCID 23668193Sodium Nitrite

Product 1

HCID 54388129O-[3(R)-acetoxy-2-diazo-1-oxobutyl]-N-trifluoroacetyl-L-serineYield 3.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of O-[3(R)-acetoxy-2(S)-amino-1-oxobutyl]-N-trifluoroacetyl-L-serine (200 mg) and chloroacetic acid (0.015 ml) in water (2ml) was added sodium nitrite (80 mg) at room temperature. After stirring for 0.5 hour at room temperature, acetic acid was added and the mixture was extracted with ethyl acetate (3 times) and the ethyl acetate extracts were combined and washed with brine. After drying over sodium sulfate, the ethyl acetate extract was filtered and concentrated. The residue was chromatographed on preparative thin layer chromatography to give O-[3(R)-acetoxy-2-diazo-1-oxobutyl]-N-trifluoroacetyl-L-serine (8 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3 times)
  2. washwashed with brine
  3. dry with materialAfter drying over sodium sulfate
  4. extractionthe ethyl acetate extract
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on preparative thin layer chromatography

Sources & evidence

ORD record
ord-514e5ae620bb410da55e1fc812916837
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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