Oxalic Acid → HCID 15297816, compound

HRID 1720469Notes

Reaction equation

HRID 1720469 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:32][CH2:31][CH2:30][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:29])[CH2:21][S:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C1CCC(N=C=NC2CCCCC2)CC1.C(O)(=O)C(O)=O>CS(C)=O.C1C=CC=CC=1.CO.O.C(OCC)(=O)C.N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:32][CH2:31][CH2:30][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:29])[CH2:21][S:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

11

Reactant 4

HCID 971Oxalic AcidHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 15297815HCID 15297815, compound

Product 1

HCID 15297816HCID 15297816, compoundYield 79%

Reagents, catalysts & solvents 6

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(phenylthio)ethyl]pyrrolidine (908 mg) was dissolved in DMSO (3 ml) and benzene (3 ml), and thereto were added pyridine (162 μl), trifluoroacetic acid (78 μl) and DCC (1.24 g) in order, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate (50 ml) was added to the reaction mixture, and oxalic acid (540 mg) in methanol (5 ml) was added thereto, followed by stirring for 30 minutes. Water (50 ml) was added to the reaction mixture and the resultant dicyclohexylurea was filtered off. The filtrate was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and saturated brine in order, and dried over magnesium sulfate, followed by concentration. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 714 mg of (2S)-1-(N-benzyloxycarbonyl-L-prolyl)-2-[(Phenylthio) acetyl]pyrrolidine (See Table 1).

Workup

  1. additionwas added
  2. stirringby stirring for 30 minutes
  3. filtrationthe resultant dicyclohexylurea was filtered off
  4. washThe filtrate was washed with 1N hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium bicarbonate and saturated brine in order, and dried over magnesium sulfate
  6. concentrationfollowed by concentration
  7. customThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

Sources & evidence

ORD record
ord-4c7a16ac25a44d969d08619bb88421f2
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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