HCID 22851712, compound → HCID 22851693, compound

HRID 55459Notes

Reaction equation

HRID 55459 reaction equation
[C:1]([NH:4][C:5]1[C:6]([O:8][C@@H:9]([CH3:16])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:7])(=[O:3])[CH3:2]>C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:1]([NH:4][C@@H:5]1[C@H:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C@H:9]([CH3:16])[O:8][C:6]1=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 22851712HCID 22851712, compound

Product 1

HCID 22851693HCID 22851693, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

0.45 g of rhodium/Al2O3 catalyst is added to 15 g of (S)-2-acetamido-3-ethoxycarbonyl-2-penten-4-olide dissolved in 100 ml of ethyl acetate and the whole is hydrogenated at 50° C. and 50 bars for 21 hours and worked up as in Example 14. The ratio of the diastereoisomers of the crude product exhibited by HPLC analysis is (2R,3S,4S):(2S,3R,4S):(2R,3R,4S)=approximately 85:13:2. Diastereoisomerically pure title compound is obtained by crystallisation from ethyl acetate, [α]D20 =-183.2° (3% in CHCl3), m.p. 165°-167° C.

Workup

  1. customis hydrogenated at 50° C.

Sources & evidence

ORD record
ord-375ecb3630cc46b09b755aefa78342ef
Source dataset
uspto-grants-1997_04
Patent number
US05625059

Reaction notes

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