1-Amino-3-(benzyloxy)propan-2-ol → 5-{4-[2-(3-Benzyloxy-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dione

HRID 1901667Notes

Reaction equation

HRID 1901667 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:13])[CH2:11][NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[C:15]([CH3:32])[CH2:16][O:17][C:18]1[CH:31]=[CH:30][C:21]([CH2:22][CH:23]2[S:27][C:26](=[O:28])[NH:25][C:24]2=[O:29])=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:8][CH2:9][CH:10]([OH:13])[CH2:11][NH:12][CH:15]([CH3:32])[CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][CH:23]2[S:27][C:26](=[O:28])[NH:25][C:24]2=[O:29])=[CH:30][CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3427951-Amino-3-(benzyloxy)propan-2-olHCID 5003444Sodium cyanoborohydrideHCID 218321505-[4-(2-Oxopropoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 153839555-{4-[2-(3-Benzyloxy-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dioneYield 11.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Example 2 was repeated, except that 545 mg of 3-benzyloxy-2-hydroxypropylamine (prepared as described in Preparation 48), 700 mg of 5-[4-(2-oxopropoxy)benzyl]thiazolidine-2,4-dione, 470 mg of sodium cyanoborohydride and 60 ml of anhydrous methanol were used. The resulting crude product was applied to a silica gel chromatography column, and eluted using a gradient elution method, with mixtures of ethyl acetate and ethanol in ratios ranging from 10:1 to 5:1 by volume as the eluent. The resulting product was further purified by reverse phase preparative high performance liquid chromatography [YMC-Pack ODS-A (trade name, manufactured by YMC Co.), using a 50:50:1:1 by volume mixture of acetonitrile, water, acetic acid and triethylamine as the eluent], to give 130 mg of the title compound as a pale yellow glassy solid having an Rf value of 0.16 (on silica gel thin layer chromatography, using a 10:1 by volume mixture of ethyl acetate and ethanol as the developing solvent).

Workup

  1. washeluted
  2. washa gradient elution method
  3. customThe resulting product was further purified by reverse phase preparative high performance liquid chromatography [YMC-Pack ODS-A (trade name, manufactured by YMC Co.)
  4. additionby volume mixture of acetonitrile, water, acetic acid and triethylamine as the eluent],

Sources & evidence

ORD record
ord-714f47cb17be48de92ff87017325afcd
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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