Hydrochloric Acid → (r/s)-4-Hydroxymethyl-4-[2-(4-octyl-phenyl)-ethyl]-oxazolidin-2-one

HRID 600193Notes

Reaction equation

HRID 600193 reaction equation
Cl[C:2](OCC1C=CC=CC=1)=[O:3].[CH3:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]([NH2:33])([CH2:31][OH:32])[CH2:29][OH:30])=[CH:24][CH:25]=1.Cl.Cl>[OH-].[Na+]>[OH:32][CH2:31][C:28]1([CH2:27][CH2:26][C:23]2[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12])=[CH:25][CH:24]=2)[CH2:29][O:30][C:2](=[O:3])[NH:33]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 10387Benzyl chloroformate2×HCID 107969Fingolimod Hydrochloride

Product 1

HCID 11302056(r/s)-4-Hydroxymethyl-4-[2-(4-octyl-phenyl)-ethyl]-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Benzyl chloroformate (0.45 ml; 3.2 mmol) is added to a suspension of FTY720.HCl (1.03 g, 3 mmol) in 2N NaOH (20 ml). The reaction is kept at RT over night and in order to complete the reaction further benzyl chloroformate (0.9 ml; 6.4 mmol) is added. After 2 days at RT the reaction is acidified with 1N HCl, extracted with methylenechloride and purified on a silica gel column using methylenechloride/methanol/acetic acid50% (9/1/0.125) as mobile phase.

Workup

  1. waitThe reaction is kept at RT over night and in order
  2. additionis added
  3. extractionextracted with methylenechloride
  4. custompurified on a silica gel column

Sources & evidence

ORD record
ord-79f8aebc3e604bd7a57e97c90de81699
Source dataset
uspto-grants-2011_03
Patent number
US07902175B2

Reaction notes

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