Hydrochloric Acid → HCID 18594801, compound

HRID 1580236Notes

Reaction equation

HRID 1580236 reaction equation
[N:1]([CH:4]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:5][CH2:6][C@@H:7]1[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])[C:10](=[O:23])[CH2:9][CH2:8]1)=[N+:2]=[N-:3].CO.O.[OH-].[K+].Cl>CCOCC>[N:1]([CH:4]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:5][CH2:6][C@@H:7]1[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:10](=[O:23])[CH2:9][CH2:8]1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18594802HCID 18594802, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 18594801HCID 18594801, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 880 mg. of ethyl 15-azido-9-oxoprostanoate (Example 110) in 15 ml. of methanol-water (1:1) containing 360 mg. of potassium hydroxide is stirred at ambient temperature for 18 hours. The resulting solution is acidified with dilute hydrochloric acid and the oily layer is taken up in ether. The ether is washed with saturated sodi sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 797 mg. (98%) of an oil; λmax. 3.0-3.5 broad (acid group), 4.88 (azido group), 5.78 and 5.90 (carbonyl groups).

Workup

  1. additionA suspension of 880 mg
  2. washThe ether is washed with saturated sodi sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customto give 797 mg

Sources & evidence

ORD record
ord-a2501d6f5b5147399d3794da20a3421d
Source dataset
uspto-grants-1976_01
Patent number
US03932472

Reaction notes

Loading…