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Water → (2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-[4-(hydroxymethyl)thiazol-2-ylthio]acetamide

HRID 545116
Notes
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Reaction equation

HRID 545116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:27])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([C:22](OCC)=[O:23])[N:21]=2)[CH2:7]1.[BH4-].[Na+].[Cl-].[Li+].O>C(O)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:27])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][OH:23])[N:21]=2)[CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 67170480(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-[4-(ethoxycarbonyl)thiazol-2-ylthio]acetamide

Product 1

HCID 67169032(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-[4-(hydroxymethyl)thiazol-2-ylthio]acetamide

Reagents, catalysts & solvents

2
HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The resultant product (2.09 g) of (1-4) was dissolved in ethanol (40 mL) and tetrahydrofuran (40 mL), sodium borohydride (454 mg) was added, lithium chloride (509 mg) was further added, and the mixture was stirred at room temperature for 4.5 hrs. Water was poured into the reaction mixture, the organic solvent alone was evaporated under reduced pressure, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (1.53 g) as a colorless oil.

Workup

  1. customthe organic solvent alone was evaporated under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography
  7. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-68192e9e3f15496c865c398a31247201
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935700B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes