Hydrochloric Acid → HCID 68696649, compound

HRID 1990899Notes

Reaction equation

HRID 1990899 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[O:12][C:11]([NH:14][CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([O:29][CH2:30][CH3:31])[CH:23]=4)[CH2:17][CH2:16]3)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-].O.Cl>C1COCC1.CO>[CH2:30]([O:29][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[CH3:28])[CH2:21][N:18]1[CH2:17][CH2:16][CH:15]([NH:14][C:11]2[O:12][C:13]3[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=[CH:8][C:9]=3[N:10]=2)[CH2:20][CH2:19]1)[CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 68700128HCID 68700128, compound

Product 1

HCID 68696649HCID 68696649, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-[1-(3-ethoxy-4-methyl-benzyl)-piperidin-4-ylamino]-benzooxazole-7-carboxylic acid methyl ester (22.0 mg, 52.0 mmol, 1.0 equiv; example 308/step 3) in a 1:1 mixture of THF/methanol (0.26 mL) was added a 1 M solution of LiOH in water (0.13 mL, 130.0 mmol, 2.5 equiv). After stirring for 18 h at rt, the pH of the reaction mixture was adjusted to 3.5 by addition of 1 M solution of HCl, the solution extracted with ethyl acetate (2×1 mL) and the combined organic phases washed with water (2×1 mL) and a conc. solution of sodium chloride (1 mL). The organic phase was dried over MgSO4, concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with ethyl acetate/acetone/acetic acid/water (6:2:1:1) providing 21.0 mg (96%) of the title compound. MS (ISP): 410.3 [M+H]+.

Workup

  1. extractionthe solution extracted with ethyl acetate (2×1 mL)
  2. washthe combined organic phases washed with water (2×1 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customthe crude reaction product
  6. custompurified with column chromatography on silica eluting with ethyl acetate/acetone/acetic acid/water (6:2:1:1)

Sources & evidence

ORD record
ord-0a363830fae244258bb2a6f64d8a5d3d
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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