Hydrochloric Acid → HCID 54398682, compound

HRID 918275Notes

Reaction equation

HRID 918275 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=O)[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1.[O:18]([C@@H:20]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]([OH:23])=[O:22])[NH2:19].CO.Cl>C(OCC)(=O)C.N1C=CC=CC=1>[OH:1][C@@H:2]1[CH2:6][C:5](=[N:19][O:18][CH:20]([C:21]([OH:23])=[O:22])[CH2:24][CH:25]([CH3:27])[CH3:26])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1.[OH:1][C@H:2]1[CH2:6][C:5](=[N:19][O:18][CH:20]([C:21]([OH:23])=[O:22])[CH2:24][CH:25]([CH3:27])[CH3:26])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3912664NorprostolHCID 18595170HCID 18595170, compound

Product 2

HCID 54398682HCID 54398682, compoundHCID 54398683HCID 54398683, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture consisting of 0.240 part of methyl 3(RS)-hydroxy-5-oxocyclopent-1-eneheptanoate, 0.200 part of 2(S)- aminoxyisocaproic acid and 4 parts of methanol is treated with 0.5 part of pyridine. That mixture is allowed to stand at room temperature for about 16 hours and then is poured into 45 parts of ethyl acetate and 20 parts by volume of 0.5 N hydrochloric acid. The ethyl acetate layer is separated, washed with water and dried over anhydrous sodium sulfate. The solvent is removed by evaporation under reduced pressure and the residue is chromatographed on silica gel using 1% ethyl acetate in chloroform as eluent to afford successive fractions of methyl 3(R)-hydroxy-5[(1-carboxyisoamyl)oxyimino]cyclopent-1-eneheptanoate, melting at about 62°-63° and methyl 3(S)-hydroxy-5-[(1-carboxyisoamyl)oxyimino]cyclopent-1-eneheptanoate.

Workup

  1. customThe ethyl acetate layer is separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent is removed by evaporation under reduced pressure
  5. customthe residue is chromatographed on silica gel using 1% ethyl acetate in chloroform as eluent

Sources & evidence

ORD record
ord-34a062487587414d9b0827d85f304879
Source dataset
uspto-grants-1976_07
Patent number
US03970683

Reaction notes

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