HCID 18639977, compound → HCID 54245672, compound

HRID 2165244Notes

Reaction equation

HRID 2165244 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH:9]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:10]([O:12][CH2:13][C@@H:14]([C:22]([OH:24])=[O:23])[NH:15]C(=O)C(F)(F)F)=[O:11].[N:30]([O-])=O.[Na+]>O>[N+:8](=[C:9]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:10]([O:12][CH2:13][C@@H:14]([C:22]([OH:24])=[O:23])[NH2:15])=[O:11])=[N-:30]

Participants

4

Reactant 2

HCID 18639977HCID 18639977, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 54245672HCID 54245672, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of O-(2-amino-4,4,4-trifluoro-1 -oxobutyl)-N-trifluoroacetyl-L-serine trifluoroacetate (500 mg) in water (5 ml) was added sodium nitrite (146 mg) at room temperature. After stirring for 30 minutes at room temperature, the reaction mixture was neutrized with 2M tris buffer solution to pH 7.0 to 7.3 and Acylase I (acylase, Sigma A-7264, made by Sigma Chemicals) (70 mg) was added. After stirring for 6 hours at room temperature, the mixture was chromatographed on SP (trade mark, made by MITSUBISHI CHEMICAL INDUSTRIES LTD.) (50 ml) eluting successively with water and a 9:1 mixture of water and acetone to give a crude product, which was chromatographed on preparative thin layer chromatography eluting with a 65:25:4 mixture of chloroform, methanol and water to give O-(2-diazo-4,4,4-trifluoro-1-oxobutyl)-L-serine (28 mg).

Workup

  1. additionwas added
  2. stirringAfter stirring for 6 hours at room temperature
  3. customthe mixture was chromatographed on SP (trade mark, made by MITSUBISHI CHEMICAL INDUSTRIES LTD.) (50 ml)
  4. washeluting successively with water
  5. additiona 9:1 mixture of water and acetone
  6. customto give a crude product, which
  7. customwas chromatographed on preparative thin layer chromatography
  8. washeluting with a 65:25:4 mixture of chloroform, methanol and water

Sources & evidence

ORD record
ord-c545494d89134040ab42925ab4023e05
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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