HCID 15034952, compound → HCID 15034953, compound

HRID 703276Notes

Reaction equation

HRID 703276 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][CH2:6][CH:7]([C:12](=[O:14])[CH3:13])[C:8]([O:10][CH3:11])=[O:9])=[O:4]>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:5][CH2:6][C@@H:7]([C@H:12]([OH:14])[CH3:13])[C:8]([O:10][CH3:11])=[O:9])=[O:4]

Participants

3

Reactant 1

HCID 15034952HCID 15034952, compound

Product 1

HCID 15034953HCID 15034953, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 ml-volume stainless steel autoclave whose atmosphere had been displaced with nitrogen was added a solution of 2.21 g (10 mmole) of methyl 2-(N-chloroacetylamino)methyl-3-oxobutanoate and 180 mg (0.1 mmol) of Ru2Cl4 ((+)-T-BINAP)2NEt3 in 20 ml of methylene chloride, and a reaction was conducted at 50° C. under a hydrogen pressure of 100 kg/cm2 for 20 hours. The reaction mixture was concentrated under reduced pressure of 20 mmHg and purified by silica gel chromatography using a 8/2 (by volume) mixture of hexane and isopropanol as an eluent to obtain 1.78 g (yield: 80%) of methyl (2S, 3R)-2-(N-chloroacetylamino)methyl-3-hydroxybutanoate having an optical purity of 95 %ee as determined in the same manner as in Example 2.

Workup

  1. customwas conducted at 50° C. under a hydrogen
  2. customfor 20 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure of 20 mmHg
  4. custompurified by silica gel chromatography
  5. additiona 8/2 (by volume) mixture of hexane and isopropanol as an eluent

Sources & evidence

ORD record
ord-0be96bb8684148a98d76f7d4b853d0fe
Source dataset
uspto-grants-1991_01
Patent number
US04981992

Reaction notes

Loading…