Chloroacetic Acid → HCID 54075419, compound

HRID 2165242Notes

Reaction equation

HRID 2165242 reaction equation
[NH2:1][C@H:2]([C:6]([O:8][CH2:9][CH2:10][C@@H:11]([C:19]([OH:21])=[O:20])[NH:12]C(=O)C(F)(F)F)=[O:7])[C@@H:3]([CH3:5])[OH:4].ClCC(O)=O.[N:27]([O-])=O.[Na+]>O>[N+:1](=[C:2]([C@H:3]([OH:4])[CH3:5])[C:6]([O:8][CH2:9][CH2:10][C@@H:11]([C:19]([OH:21])=[O:20])[NH2:12])=[O:7])=[N-:27]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 23668193Sodium NitriteHCID 54035009HCID 54035009, compound

Product 1

HCID 54075419HCID 54075419, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of O-L-threonyl-N-trifluoroacetyl-L-homoserine (800 mg) and 4M aqueous chloroacetic acid (100 μl) in water (10 ml) was added sodium nitrite (345 mg) at room temperature. After stirring for 15 minutes at room temperature, the reaction mixture was neutrized with 2M tris buffer solution to pH 7.0 to 7.3 and then Acylase I (acylase, Sigma A-7264, made by Sigma Chemicals) (100 mg) was added. The mixture was stirred for 5 hours at 35° C. and chromatographed on carbon (50 ml) eluting successively with water and a 9:1 mixture of water and acetone to give O-[2-diazo-3(R)-hydroxy-1-oxobutyl]-L-homoserine (28 mg).

Workup

  1. additionAcylase I (acylase, Sigma A-7264, made by Sigma Chemicals) (100 mg) was added
  2. stirringThe mixture was stirred for 5 hours at 35° C.
  3. customchromatographed on carbon (50 ml)
  4. washeluting successively with water
  5. additiona 9:1 mixture of water and acetone

Sources & evidence

ORD record
ord-477bfbe37baf4067a32ab23dadb5aff0
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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