Water → HCID 86745148, compound

HRID 345235Notes

Reaction equation

HRID 345235 reaction equation
C([C:5](O[SiH](C)C)([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]1[C@@H:19]([CH:20]=[CH:21][CH2:22][C:23]([CH3:30])([O:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:17][C:16]1=[O:31])[C:6]([O:8][CH3:9])=[O:7])CCC.C1C[O:39]CC1.[OH2:41]>CC(O)=O.O>[OH:41][C@H:18]1[C@H:19]([CH:20]=[CH:21][C@@H:22]([OH:39])[C@:23]([CH3:30])([O:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])[C@@H:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:5][C:6]([O:8][CH3:9])=[O:7])[C:16](=[O:31])[CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 131717030HCID 131717030, compound

Product 1

HCID 86745148HCID 86745148, compound

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A mixture of (8R,11R,12R,15R,16R)11,15-di-t.butyl-dimethylsilyloxy-16-methyl-16-methoxy-9 -oxo-prost-13-en-1-oic acid, methyl ester (0.045 g, 0.07 mmol) in 0.5 ml of HOAc/H2O)/THF: 3/1/1) was stirred for 48 h at room temperature. After adding more water (5 ml), the mixture was neutralized by addition of an aqueous solution of Na2HPO4, and extracted with Et2O (2×10 ml). The combined organic layers were washed with aqueous NaHCO3, water and then brine, dried (MgSO4) and flash evaporated to afford crude (8R,11R,12R,15R,16R)11,15-Dihydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid, methyl ester. Final purification was achieved by chromatography on 10 g of silicagel (eluant EtOAc).

Workup

  1. additionA mixture of (8R,11R,12R,15R,16R)11,15-di-t
  2. extractionextracted with Et2O (2×10 ml)
  3. washThe combined organic layers were washed with aqueous NaHCO3, water
  4. dry with materialbrine, dried (MgSO4) and flash
  5. customevaporated

Sources & evidence

ORD record
ord-65595fef1c1c422fb6e0b89ef357448b
Source dataset
uspto-grants-1991_10
Patent number
US05055592

Reaction notes

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