Hydrochloric Acid → HCID 131724266, compound

HRID 433835Notes

Reaction equation

HRID 433835 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:17]=[C:16]([CH2:18][CH:19]([N:25]=C(C2C=CC=CC=2)C2C=CC=CC=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[O:15][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[ClH:44]>C(OCC)(=O)C>[ClH:44].[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:17]=[C:16]([CH2:18][CH:19]([NH2:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[O:15][N:14]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20610320HCID 20610320, compound

Product 1

HCID 131724266HCID 131724266, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-{5-[2-(Benzhydrylidene-amino)-2-ethoxycarbonyl-ethyl]-isoxazol-3-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (700 mg, 1.35 mmol) was stirred in a mixture of ethyl acetate (20 mL) and 1N hydrochloric acid (100 mL) for 3 hours. The reaction was neutralized by the addition of saturated sodium bicarbonate. The aqueous portion was extracted with diethyl ether. The combined organics were dried over magnesium sulfate and the solvent removed in vacuo. The resulting oil (200 mg) was used directly in example 14C.

Workup

  1. extractionThe aqueous portion was extracted with diethyl ether
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d306edd80dc44ab3a624bd7616d4774b
Source dataset
uspto-grants-2003_12
Patent number
US06668527B2

Reaction notes

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