1,4-Dioxane--water (1/1) → HCID 22862579, compound

HRID 1735411Notes

Reaction equation

[N+](=[CH:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([C@@H:13]1[CH2:17][S:16][CH2:15][N:14]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:12])=[O:5])=[N-].[O:28]1CCOCC1.O>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[OH:28][CH2:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([C@@H:13]1[CH2:17][S:16][CH2:15][N:14]1[C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])=[O:12])=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

1,4-Dioxane-water (5 ml-5 ml) was added to the crude (R)-4[[(S)-2-(diazoacetyl)-1-pyrrolidinyl]carbonyl]-3-(phenylmethyloxycarbonyl)thiazolidine (970 mg) and copper sulfate pentahydrate (several mg), and the mixture was heated at 100° C. for 0.5 hour. 1,4-Dioxane was distilled away under reduced pressure and a saturated sodium hydrogencarbonate was added. The mixture was extracted with ethyl acetate. The extract was washed with 10% citric acid and saturated brine in order, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (eluent: chloroform - methanol) to give the title compound (92 mg) (see Table 4).

Workup

distillation1,4-Dioxane was distilled away under reduced pressure
additiona saturated sodium hydrogencarbonate was added
extractionThe mixture was extracted with ethyl acetate
washThe extract was washed with 10% citric acid and saturated brine in order
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-5b91e16ca2ae4434821bb2ee472643ca
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05536737

Reaction notes

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