Methyl 4-chloroacetoacetate → Methyl (R)-4-Chloro-3-hydroxybutyrate

HRID 985933Notes

Reaction equation

HRID 985933 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5]([CH2:7][Cl:8])=[O:6].C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[CH3:1][O:2][C:3](=[O:9])[CH2:4][C@@H:5]([OH:6])[CH2:7][Cl:8]

Participants

4

Reactant 2

HCID 36240Methyl 4-chloroacetoacetateHCID 439153Nadh

Product 1

HCID 10920707Methyl (R)-4-Chloro-3-hydroxybutyrate

Reagents, catalysts & solvents 1

HCID 24243Trisodium PhosphateSolvent

Procedure

Methyl-4-chloroacetoacetate (VII) (100 mg) was incubated with 29 units of porcine heart (EC 1.1.1.35), B-hydroxyacyl CoA dehydrogenase (Sigma, H4626), and 1.36 g of NADH (Sigma, 90%) in 30 ml of 0.1 M sodium phosphate buffer, pH 6.5.

Sources & evidence

ORD record
ord-57a389a067644a3f99aec4750d3b1ed5
Source dataset
uspto-grants-1987_12
Patent number
US04710468

Reaction notes

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