Hydrochloric Acid → 1-(3-(2-(5,5-Bis(carboxymethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoyl)piperidine-4-carboxylic acid

HRID 1486906Notes

Reaction equation

HRID 1486906 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][C:5]1([CH2:32][C:33](=[O:36])[O:34]C)[O:9][N:8]=[C:7]([C:10]2[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:11]=2[CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH:24]([C:27]([O:29]CC)=[O:28])[CH2:23][CH2:22]2)=[O:20])[CH2:6]1.C1COCC1.[OH-].[Na+].Cl>CO>[C:33]([CH2:32][C:5]1([CH2:4][C:3]([OH:37])=[O:2])[O:9][N:8]=[C:7]([C:10]2[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:11]=2[CH2:17][CH2:18][C:19]([N:21]2[CH2:22][CH2:23][CH:24]([C:27]([OH:29])=[O:28])[CH2:25][CH2:26]2)=[O:20])[CH2:6]1)([OH:36])=[O:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118292833Ethyl 1-(3-(2-(5,5-bis(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoyl)piperidine-4-carboxylate

Product 1

HCID 1182928111-(3-(2-(5,5-Bis(carboxymethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoyl)piperidine-4-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 1-(3-(2-(5,5-bis(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoyl)piperidine-4-carboxylate (760 mg), THF (8 mL), methanol (8 mL), and a 1 M aqueous sodium hydroxide solution (8 mL) was stirred at room temperature for 2 hours. The reaction mixture was rendered acidic using 6 M hydrochloric acid at 0 C, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure to obtain the title compound (664 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bbd51ee5d38a4cf5996e36e053b95e00
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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