Hydrochloric Acid → HCID 66657884, compound

HRID 420611Notes

Reaction equation

HRID 420611 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]3[S:21][C:22]4[CH:28]=[C:27]([O:29][C:30]([F:33])([F:32])[F:31])[CH:26]=[CH:25][C:23]=4[N:24]=3)[C@H:16]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:15]2)[CH:7]=1.[OH-].[Na+].O1CCCC1.Cl>C(Cl)(Cl)Cl.O.CO>[CH2:34]([C@H:16]1[N:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27]([O:29][C:30]([F:32])([F:33])[F:31])[CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:18][CH2:19][N:14]([CH2:13][C:8]2[CH:7]=[C:6]([CH:11]=[C:10]([CH3:12])[CH:9]=2)[O:5][CH2:4][C:3]([OH:38])=[O:2])[CH2:15]1)[CH2:35][CH2:36][CH3:37]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66658097HCID 66658097, compound

Product 1

HCID 66657884HCID 66657884, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of [3-[(R)-3-butyl-4-(6-trifluoromethoxybenzothiazole-2-yl)-piperazine-1-ylmethyl]-5-methylpheno xy]acetic acid methyl ester (203 mg), 2N sodium hydroxide (0.46 mL), tetrahydrofuran (2 mL) and methanol (2 mL) was stirred at room temperature for 16 hours. To the reaction solution were added water and chloroform. The mixture was neutralized with 2N hydrochloric acid. The reaction solution was extracted with chloroform. The organic layer was washed with brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give the title compound (182 mg). Yield: 91%.

Workup

  1. extractionThe reaction solution was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f881d03fed3343348c2568e0d437806a
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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