67040-53-3 → HCID 70552483, compound

HRID 1105645Notes

Reaction equation

HRID 1105645 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](=[O:41])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C@@H:24]2[C@@H:28]([S:29][CH2:30][C:31]([OH:38])([CH3:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C@H:27]([OH:39])[CH2:26][C:25]2=[O:40])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17](=[O:41])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C@@H:24]2[C@@H:28]([S:29][CH2:30][C:31]([OH:38])([CH3:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C@H:27]([OH:39])[CH2:26][CH:25]2[OH:40])=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 7217467040-53-3

Product 1

HCID 70552483HCID 70552483, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen, 1.3 g. of 11α,15-dihydroxy-15-methyl-9-oxo-13-thiaprostanoic acid p-benzoylaminophenyl ester, dissolved in 40 ml. of dry THF was added to a suspension of 3.3 g. of LiAl(O-tert.--C4H9)3H in 25 ml. of dry THF. The solution was allowed to stand for 1 hour at room temperature; then poured into 90 ml. of ice-cold 1 N HCl; and extracted with CHCl3. The organic phase was washed with water and dried over NaSO4. The solvent was distilled off. After chromatographic purification of the residue (silica gel/ethyl acetate), 9,11α,15-trihydroxy-15-methyl-13-thiaprostanoic acid p-benzoylaminophenyl ester was obtained.

Workup

  1. additionthen poured into 90 ml
  2. extractionand extracted with CHCl3
  3. washThe organic phase was washed with water
  4. dry with materialdried over NaSO4
  5. distillationThe solvent was distilled off
  6. customAfter chromatographic purification of the residue (silica gel/ethyl acetate)

Sources & evidence

ORD record
ord-ec0f0117b0c04d96a1c2a26644982f08
Source dataset
uspto-grants-1982_01
Patent number
US04309441

Reaction notes

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