Hydrochloric Acid → HCID 57673909, compound

HRID 490058Notes

Reaction equation

HRID 490058 reaction equation
[NH2:1][C:2]([CH2:25][OH:26])([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=1)[CH2:3][O:4][P:5](=[O:8])([OH:7])[OH:6].C(N([CH2:43][C:44]([OH:46])=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.B(O)(O)O.Cl>C(O)C>[OH:26][CH2:25][C:2]([N:1]1[CH2:12][C:11]2[C:43](=[CH:3][CH:2]=[CH:9][CH:10]=2)[C:44]1=[O:46])([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][CH:16]=1)[CH2:3][O:4][P:5](=[O:6])([OH:7])[OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6049Ethylenediaminetetraacetic AcidHCID 7628Boric AcidHCID 9908268Fingolimod phosphate

Product 1

HCID 57673909HCID 57673909, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The endproduct of step d) ((R/S)-FTY720-phosphate) (50 mg; 0.125 mmol) is suspended in a solution of EDTA (0.5 ml; 10 mM in water) and aqueous boric acid (0.5 ml; 3% in water; adjusted to pH 10.5 with aqueous KOH10%). After addition of OPA (33 mg, 0.25 mmol), dissolved in ethanol (0.5 ml), the reaction is kept at RT for 1 hour (ultrasound). After that the pH is adjusted to 3.5 (aqueous HCl; 1N) and extracted with ethylacetate (three times). The organic layer is dried over Na2SO4 and the compound is purified on silica gel using methylenechloride/methanol (95/5→0/100) as mobile phase.

Workup

  1. additionAfter addition of OPA (33 mg, 0.25 mmol)
  2. extractionextracted with ethylacetate (three times)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. customthe compound is purified on silica gel

Sources & evidence

ORD record
ord-3686e9d92cd049048910744240f2e15e
Source dataset
uspto-grants-2009_05
Patent number
US07528120B2

Reaction notes

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