Hydrogen chloride-ethyl acetate → HCID 66680322, compound

HRID 1626733Notes

Reaction equation

HRID 1626733 reaction equation
Cl.C(OCC)(=O)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2C(OC(C)(C)C)=O)=[O:17])=[C:11]([C:30]([O:32][CH3:33])=[O:31])[CH:10]=1>C(OCC)(=O)C>[ClH:8].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:17])[C@@H:18]2[CH2:22][CH2:21][CH2:20][NH:19]2)=[C:11]([CH:10]=1)[C:30]([O:32][CH3:33])=[O:31]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66681229HCID 66681229, compound

Product 1

HCID 66680322HCID 66680322, compoundYield 196.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4N hydrogen chloride/ethyl acetate (10 mL) was added to an ethyl acetate (10 mL) solution comprising 1.40 g (3.66 mmol) of tert-butyl (2S)-2-{[4-chloro-2-(methoxycarbonyl)phenyl]carbamoyl}pyrrolidine-1-carboxylate at 0° C., and the mixture was stirred at room temperature for 5 hours. After the reaction mixture was condensed, IPE was added to the residue, and white solids were collected by filtration, washed with IPE, and dried under reduced pressure at room temperature, thereby giving 1.15 g of methyl 5-chloro-2-(L-prolylamino)benzoate hydrochloride (yield: 98%).

Workup

  1. customcondensed, IPE
  2. additionwas added to the residue, and white solids
  3. filtrationwere collected by filtration
  4. washwashed with IPE
  5. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-7d5b021b6ed04db1a791eaa728c2ead3
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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