Pyridine → HCID 70391501, compound

HRID 247506Notes

Reaction equation

HRID 247506 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14]([C@@H:15]([OH:25])/[CH:16]=[CH:17]/[C:18]([CH3:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([CH3:26])[CH2:12][C:11]1=[O:27].N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14]([C@@H:15]([O:25][C:35](=[O:37])[CH3:36])/[CH:16]=[CH:17]/[C:18]([CH3:23])([CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([CH3:26])[CH2:12][C:11]1=[O:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 70391665HCID 70391665, compound

Product 1

HCID 70391501HCID 70391501, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the crude optically active (5Z,11alpha,13S,14E)-13-(hydroxy)-11,16,16-trimethyl-9-oxoprosta-5,14-dien-1-oic acid methyl ester (9.2 g) in methylene chloride (100 mL) was treated with pyridine (5.5 mL) and 4-dimethylaminopyridine (0.5 g), cooled to 0°, and treated with acetic anhydride (3.4 mL). The resulting mixture was stirred overnight at room temperature and then washed with 2N HCL, water, NaHCO3 solution, and brine (75 mL of each). After drying over sodium sulfate, the solvent was stripped off leaving 9.7 g (~100%) of crude optically active (5Z,11alpha,13S,14E)-13-(acetyloxy)-11,16,16-trimethyl-9-oxoprosta-5,14-dien-1-oic acid methyl ester as a yellow oil. This material was used as is in Example XXII.

Workup

  1. temperaturecooled to 0°
  2. washwashed with 2N HCL, water, NaHCO3 solution, and brine (75 mL of each)
  3. dry with materialAfter drying over sodium sulfate

Sources & evidence

ORD record
ord-180fe896156d464c97a82215d4a3535b
Source dataset
uspto-grants-1987_11
Patent number
US04707555

Reaction notes

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