Ethyl Acetate → HCID 66836089, compound

HRID 2404451Notes

Reaction equation

HRID 2404451 reaction equation
CO[C:3]([C:5]1([CH2:8][S:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([C:25]3[S:26][C:27]4[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=4[N:29]=3)[O:17][CH:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH:11]=2)[CH2:7][CH2:6]1)=O.[Li].[C:35](OCC)(=[O:37])C.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[S:26]1[C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=[C:25]1[CH:16]([O:17][CH:18]1[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]1)[C:12]1[CH:11]=[C:10]([S:9][CH2:8][C:5]2([CH2:3][CH2:35][OH:37])[CH2:6][CH2:7]2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 3028194LithiumHCID 66835895HCID 66835895, compound

Product 1

HCID 66836089HCID 66836089, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenylsulfanylmethyl}cyclopropanecarboxylic acid methyl ester (56 mg) in tetrahydrofuran (5 mL) is added lithium aluminumhydride (25 mg) at 0° C. The reaction mixture is allowed to reach room temperature and ethyl acetate (2 mL) is added. After stirring for 5 minutes, a half-saturated aqueous solution of sodium carbonate (6 mL) is added. The aqueous phase is extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 95/5/0.5) to afford 2-(1-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenylsulfanylmethyl}cyclopropyl)ethanol.

Workup

  1. customto reach room temperature
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 95/5/0.5)

Sources & evidence

ORD record
ord-06da22b2d2b54106a01d3fc3b071f8aa
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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