Hydrochloric Acid → HCID 19973181, compound

HRID 1901288Notes

Reaction equation

HRID 1901288 reaction equation
CC([N:5]([CH2:9][C:10]([NH:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](=[O:20])[CH3:19])=[O:11])C(=O)[O-])(C)C.[ClH:21].CCOC(C)=O.CCCCCC>C(OCC)(=O)C.C(O)(C)C>[ClH:21].[C:18]([C:14]1[N:13]([NH:12][C:10](=[O:11])[CH2:9][NH2:5])[CH:17]=[CH:16][CH:15]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 867474421,1-dimethylethyl-[2-[(2-acetyl-1H-pyrrol-1-yl)amino]-2-oxoethyl]carbamate

Product 1

HCID 19973181HCID 19973181, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution consisting of 1,1-dimethylethyl-[2-[(2-acetyl-1H-pyrrol-1-yl)amino]-2-oxoethyl]carbamate (5.90 g) in ethyl acetate (45 ml) and isopropanol (35ml) was added ethereal HCl (1.7M, excess). The resulting suspension was gently heated until the reaction mixture was homogeneous. After stirring for 24 hours at room temperature, the reaction appeared complete by TLC (silica gel, 50% EtOAc/hexane). The solid product was collected by filtration under nitrogen and recrystallized from methanol/ether to afford 3.30 g of the product, m.p. 179°-182° C.

Workup

  1. temperatureThe resulting suspension was gently heated until the reaction mixture
  2. filtrationThe solid product was collected by filtration under nitrogen
  3. customrecrystallized from methanol/ether

Sources & evidence

ORD record
ord-2c00d0da6fa8482a8f73803d2b689126
Source dataset
uspto-grants-1996_11
Patent number
US05576446

Reaction notes

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