Hydrogen Sulfide → HCID 58654421, compound

HRID 1170511Notes

Reaction equation

Cl.[CH2:2]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]([O:19][CH2:20][CH3:21])=N)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[SH2:28]>C1COCC1>[CH2:2]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]([O:19][CH2:20][CH3:21])=[S:28])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -20 °C

Procedure

2-Ethoxycarbonimidoyl-pyrrolidine-1-carboxylic acid benzyl ester hydrochloride (42.8 g, 146.0 mmol) was dissolved in THF (150 mL) and cooled to −20° C. Pyridine (80 ml) was added to the reaction and H2S was bubbled through the reaction for 60 min. The reaction's temperature was maintained at −20° C. for 2 hours while stirring. The pH was adjust to pH=4 by addition of 5M HCl. The resulting solution was transferred to a separatory funnel and extracted with diethyl ether (3×100 mL). The organic layers were combined and washed with brine (100 ml). The organic layer was dried over MgSO4 and concentrated under vacuo to afford 20.0 g (47%) of 2-ethoxythiocarbonyl-pyrrolidine-1-carboxylic acid benzyl ester as a yellow oil.

Workup

customwas bubbled through the reaction for 60 min
temperatureThe reaction's temperature was maintained at −20° C. for 2 hours
additionThe pH was adjust to pH=4 by addition of 5M HCl
customThe resulting solution was transferred to a separatory funnel
extractionextracted with diethyl ether (3×100 mL)
washwashed with brine (100 ml)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under vacuo

Sources & evidence

ORD record: ord-bf6bef877f0d408b93b209c473b480bc
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825256B2

Reaction notes

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