Diazomethane → HCID 86733393, compound

HRID 1076055Notes

Reaction equation

HRID 1076055 reaction equation
[C:1]([O:4][C@@H:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])/[CH:6]=[CH:7]/[C@@H:8]1[C@@H:12]([CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:11]=[CH:10][CH:9]1[OH:22])(=[O:3])[CH3:2].[N+](=[CH2:30])=[N-].N(CNC(N)=O)=O.[OH-].[K+]>C(O)(=O)C.C(OCC)C>[C:1]([O:4][C@@H:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])/[CH:6]=[CH:7]/[C@@H:8]1[C@@H:12]([CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:30])=[O:20])[CH:11]=[CH:10][CH:9]1[OH:22])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 104823Urea, (nitrosomethyl)-HCID 68128026HCID 68128026, compound

Product 1

HCID 86733393HCID 86733393, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

to a solution of 8 parts of (5Z,13E,15S)-15-acetyloxy-11ξ-hydroxyprosta-5,9,13-trien-1-oic acid in 175 parts of diethyl ether is added an ethereal solution of diazomethane prepared from 30 parts of N-nitrosomethylurea, 90 parts of aqueous 40% potassium hydroxide, and 210 parts of diethyl ether as described in Org. Syn., 15, 4 (1935). The resultant mixture is allowed to stand at 5° for 30 minutes, whereupon 2 parts of acetic acid is introduced and the mixture thus obtained extracted with diethyl ether. The extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residual red oil is taken up in benzene; and the benzene solution is chromatographed on silica gel, using benzene and mixtures thereof with increasing amounts of ethyl acetate as developing solvents. From an eluate comprising 30% ethyl acetate in benzene, on evaporation of solvent, methyl (5Z,13E,15S)-15-acetyloxy-11ξ-hydroxyprosta-5,9,13-trien-1-oate is obtained as a pale yellow oil.

Workup

  1. additionis introduced
  2. customthe mixture thus obtained
  3. extractionextracted with diethyl ether
  4. washThe extract is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationstripped of solvent by vacuum distillation
  7. customand the benzene solution is chromatographed on silica gel
  8. customFrom an eluate comprising 30% ethyl acetate in benzene, on evaporation of solvent

Sources & evidence

ORD record
ord-b4f427a68cdc40e795487cc3ddb152d7
Source dataset
uspto-grants-1976_05
Patent number
US03954844

Reaction notes

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