Hydrogen chloride-ethyl acetate → HCID 66638003, compound

HRID 604244Notes

Reaction equation

HRID 604244 reaction equation
[ClH:1].C(OCC)(=O)C.[CH2:8]([O:10][C:11](=[O:36])[CH2:12][NH:13][C:14](=[O:35])[CH2:15][NH:16][C:17](=[O:34])[C@H:18]([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[NH:19]C(OC(C)(C)C)=O)[CH3:9]>C(OCC)(=O)C.C(OCC)C>[ClH:1].[CH2:8]([O:10][C:11](=[O:36])[CH2:12][NH:13][C:14](=[O:35])[CH2:15][NH:16][C:17](=[O:34])[C@H:18]([CH2:27][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)[NH2:19])[CH3:9]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66637482HCID 66637482, compound

Product 1

HCID 66638003HCID 66638003, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

After 3.0 mL (12 mmol) of 4M hydrogenchloride/ethyl acetate solution was added to a solution of 506.2 mg (1.22 mmol) of N-t-butoxycarbonyl-β-cyclohexyl-L-alanyl-glycyl-glycine ethylester in ethyl acetate (1 mL) with stirring under ice cooling, the reaction mixture was stirred at room temperature for 4.5 hours. Diethyl ether (12 mL) was added to the mixture and the mixture was stirred under ice cooling. Then the precipitates were collected by filtration to obtain hygroscopic crude crystals. The crude crystals were suspended in diethyl ether (10 mL), and then collected by filtration, to give 370.3 mg of β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester hydrochloride (yield 86%) as a colorless crystalline power.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 4.5 hours
  2. stirringthe mixture was stirred under ice cooling
  3. filtrationThen the precipitates were collected by filtration
  4. customto obtain hygroscopic crude crystals
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3ca76000a7f941b48a1edf0ccb119d71
Source dataset
uspto-grants-2011_03
Patent number
US07910556B2

Reaction notes

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