Acetic Acid → HCID 21499106, compound

HRID 973198Notes

Reaction equation

HRID 973198 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][CH:5]([CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[CH2:6][CH2:7][CH2:8][N:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[S:10]([CH3:13])(=[O:12])=[O:11].C(O)(=O)C>CCOCC>[OH:4][CH:5]([CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[CH2:6][CH2:7][CH2:8][N:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:3])=[O:21])[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 214016607-{N-[4-hydroxy-5-(4-fluorophenoxy)-pentyl]methanesulfonamido}heptanoic acid

Product 1

HCID 21499106HCID 21499106, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (approximately 2.5 g., 0.06 mole) in ether (100 ml.) is mixed with a solution of 7-{N-[4-hydroxy-5-(4-fluorophenoxy)pentyl]methanesulfonamido }heptanoic acid (12.3 g., 0.03 mole) (Example 1, Step E) in ether (50 ml.). The resulting solution is allowed to stand at room temperature for 4 hours. Acetic acid is then added to destroy the excess diazomethane and the solution is washed with dilute sodium bicarbonate solution and water and dried over sodium sulfate. Evaporation of volatile materials at reduced pressure yields methyl 7-{N-[4-hydroxy-5(4-fluorophenoxy)pentyl]methanesulfonamido }heptanoate as a viscous oil.

Workup

  1. customto destroy the excess diazomethane
  2. washthe solution is washed with dilute sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of volatile materials at reduced pressure

Sources & evidence

ORD record
ord-5ddbe8a28ce74573a69721657c3d4486
Source dataset
uspto-grants-1977_10
Patent number
US04055596

Reaction notes

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