Hydrochloric Acid → [1-(Benzoylaminomethyl)-2-m-tolyloxyethyl]carbamic acid benzyl ester

HRID 12404Notes

Reaction equation

HRID 12404 reaction equation
C(O[C:6](=[O:30])[NH:7][CH2:8][CH:9]([NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1)(C)(C)C.Cl>O1CCOCC1>[CH2:23]([O:22][C:20](=[O:21])[NH:19][CH:9]([CH2:8][NH:7][C:6](=[O:30])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68698746(2-Benzyloxycarbonylamino-3-m-tolyloxypropyl)carbamic acid tert-butyl ester

Product 1

HCID 68695345[1-(Benzoylaminomethyl)-2-m-tolyloxyethyl]carbamic acid benzyl esterYield 180.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To (2-benzyloxycarbonylamino-3-m-tolyloxypropyl)carbamic acid tert-butyl ester (220 mg) obtained in Step 2 was added 4N solution (2 ml) of hydrogen chloride in dioxane, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated, dichloromethane (7 ml), benzoyl chloride (96 μl) and triethylamine (265 μl) were added to the obtained solid, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate and, after washing with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give [1-(benzoylaminomethyl)-2-m-tolyloxyethyl]carbamic acid benzyl ester (200 mg).

Workup

  1. customThe solvent was evaporated
  2. additiondichloromethane (7 ml), benzoyl chloride (96 μl) and triethylamine (265 μl) were added to the obtained solid
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. additionThe reaction mixture was diluted with ethyl acetate
  5. washafter washing with water
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe obtained crude product
  9. customwas purified by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0ad54d77cb704d8991ae751edab467d2
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Reaction notes

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