Hydrogen chloride-ethyl acetate → Methyl 2-[(4-aminobutanoyl)amino]-5-chlorobenzoate hydrochloride

HRID 1626721Notes

Reaction equation

HRID 1626721 reaction equation
Cl.C(OCC)(=O)C.C(OC([NH:15][CH2:16][CH2:17][CH2:18][C:19]([NH:21][C:22]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25])=[O:20])=O)(C)(C)C>C(OCC)(=O)C>[ClH:32].[NH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH:21][C:22]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25])=[O:20]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66680085Methyl 2-({4-[(tert-butoxycarbonyl)amino]butanoyl}amino)-5-chlorobenzoate

Product 1

HCID 66680776Methyl 2-[(4-aminobutanoyl)amino]-5-chlorobenzoate hydrochlorideYield 196.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4N hydrogen chloride/ethyl acetate was added to an ethyl acetate solution comprising 2.16 g (5.82 mmol) of methyl 2-({4-[(tert-butoxycarbonyl)amino]butanoyl}amino)-5-chlorobenzoate at 0° C., and the mixture was stirred at room temperature for 3 hours. Thereafter, IPE was added to the reaction mixture. Crystals were collected by filtration, followed by drying, thereby giving 1.76 g of methyl 2-[(4-aminobutanoyl)amino]-5-chlorobenzoate hydrochloride (yield: 99%).

Workup

  1. additionThereafter, IPE was added to the reaction mixture
  2. filtrationCrystals were collected by filtration
  3. customby drying

Sources & evidence

ORD record
ord-8db190b5a4b44eb285bcd3876d6e78b9
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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