Potassium Carbonate → HCID 12773841, compound

HRID 2058935Notes

Reaction equation

Cl.[C:2]1([C@@H:8]2[NH:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:19][CH2:20][C:21](Cl)=[O:22].[C:24]([O-:32])(=[S:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[K+].C(O)(=S)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:24]([S:31][CH2:19][CH2:20][C:21]([N:12]1[C@@H:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10][C@H:11]1[C:13]([OH:15])=[O:14])=[O:22])(=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of cis-5-phenyl proline hydrochloride (5.0 g., 0.022 m) and 1 N sodium hydroxide (44 ml.) at 10° C. was slowly added 3-bromopropionyl chloride (2.2 ml., 0.022 m) and 2-N sodium hydroxide (11 ml.), keeping pH between 7.5 and 9. The mixture was stirred at 25° C. for 3 hours. Potassium thiobenzoate, prepared by mixing thiobenzoic acid, 95% (3.28 g., 0.024 m) and potassium carbonate (2.02 g., 0.014 m) in water (25 ml.), was added to the reaction, which was stirred overnight at 25° C. The solution was acidified and extracted with ethylacetate. The extract was washed, dried over sodium sulfate and the solvent was evaporated off to yield the title compound as a gum which was employed as the reactant in the following example without further purification.

Workup

customat 10° C.
additionwas added to the reaction, which
stirringwas stirred overnight at 25° C
extractionextracted with ethylacetate
washThe extract was washed
dry with materialdried over sodium sulfate
customthe solvent was evaporated off

Sources & evidence

ORD record: ord-e0b17ec0d295456c903ee1cb4f3e0767
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04320057

Reaction notes

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