Hydrochloric Acid → HCID 22137970, compound

HRID 1884166Notes

Reaction equation

HRID 1884166 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[CH:13][CH:12]=1)(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)C>[NH2:7][CH2:8][C:9]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[CH:15][CH:16]=1)=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 10340Sodium CarbonateHCID 69008328HCID 69008328, compound

Product 1

HCID 22137970HCID 22137970, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

A slurry of 0.166 g (0.44 mmol) of {[4-(3-fluoro-benzyloxy)-phenylcarbamoyl]-methyl}-carbamic acid tert-butyl ester in 1 ml diethyl ether is treated with 3 ml of a saturated solution of gaseous hydrochloric acid in diethyl ether. The mixture is refluxed for 4 h, poured on water and made basic by addition of a saturated sodium carbonate solution. Extraction with ethyl acetate yields a yellowish solid which is dissolved in about 1 ml of diethyl ether and treated with a few drops of a saturated solution of gaseous hydrochloric acid in diethyl ether. The precipitate is filtered to give 0.051 g (37%) of a colorless solid. MS: m/e=275.2 (M++H).

Workup

  1. temperatureThe mixture is refluxed for 4 h
  2. additionpoured on water
  3. extractionExtraction with ethyl acetate
  4. customyields a yellowish solid which
  5. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-550ba57bfe4f4047897c98859f3a7745
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

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