2(S)-acetamido-3(S)-methoxycarbonyl-4(R)-pentanolide → HCID 22851699, compound

HRID 55460Notes

Reaction equation

C([NH:4][C@H:5]1[C@H:10]([C:11]([O:13]C)=[O:12])[C@@H:9]([CH3:15])[O:8][C:6]1=[O:7])(=O)C>Cl>[NH2:4][C@H:5]1[C@H:10]([C:11]([OH:13])=[O:12])[C@@H:9]([CH3:15])[O:8][C:6]1=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

114.4 g of 2(S)-acetamido-3(S)-methoxycarbonyl-4(R)-pentanolide are heated at 120° C. for 24 hours in semi-concentrated hydrochloric acid. The solution is slowly cooled to 0° C., and the precipitate is filtered off, washed with ethyl acetate, dried under a high vacuum and recrystallised from methanol. Hydrochloride of the title compound, [α]D20 =-21.5° (1% in H2O), m.p. >250° C. The free title compound is obtained by treating the hydrochloride with an excess of propylene oxide in hot methanol, [α]D20 =-23.1° (1% in 1N HCl), m.p. 196°-200° C.

Workup

filtrationthe precipitate is filtered off
washwashed with ethyl acetate
customdried under a high vacuum
customrecrystallised from methanol. Hydrochloride of the title compound, [α]D20 =-21.5° (1% in H2O), m.p. >250° C

Sources & evidence

ORD record: ord-e066bd0d3b6d493c9e819c00b51f8245
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05625059

Reaction notes

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