HCID 15034948, compound → HCID 15034949, compound

HRID 703274Notes

Reaction equation

HRID 703274 reaction equation
[C:1]([NH:4][CH2:5][CH:6]([C:12](=[O:14])[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2]>C(Cl)Cl>[C:1]([NH:4][CH2:5][C@@H:6]([C@H:12]([OH:14])[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 15034948HCID 15034948, compound

Product 1

HCID 15034949HCID 15034949, compoundYield 96.5%

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 2.01 g (10 mmole) of ethyl 2-(N-acetylamino)methyl-3-oxobutanoate and 84.5 mg (0.05 mmole) of Ru2Cl4 ((+)-BINAP)2NEt3 in 18 ml of methylene chloride, and a reaction was conducted at 35° C. under a hydrogen pressure of 70 kg/cm2 for 17 hours. The reaction mixture was taken out, concentrated under reduced pressure of 20 mmHg, and purified by silica gel column chromatography using a 7/3 (by volume) mixed solvent of hexane and isopropanol as an eluent to obtain 1.95 g (yield: 96.5%) of ethyl (2S, 3R)-2-(N-acetylamino)methyl-3-hydroxybutanoate having an optical purity of 98 %ee. The optical purity of the product was determined by HPLC in the same manner as in Example 1, except for using A-002-3 S-3 120A produced by Yamamura Kagaku Kenkyusho K.K. as a column and a 800/200/1 (by volume) mixture of hexane, tetrahydrofuran and methanol as an eluent.

Workup

  1. customwas conducted at 35° C. under a hydrogen
  2. customfor 17 hours
  3. concentrationconcentrated under reduced pressure of 20 mmHg
  4. custompurified by silica gel column chromatography
  5. additionmixed solvent of hexane and isopropanol as an eluent

Sources & evidence

ORD record
ord-dfbaac2902ea406bab9f364729377d9f
Source dataset
uspto-grants-1991_01
Patent number
US04981992

Reaction notes

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