Hydrogen chloride-ethyl acetate → HCID 66638003, compound

HRID 1093921Notes

Reaction equation

HRID 1093921 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][NH:6][C:7](=[O:28])[CH2:8][NH:9][C:10](=[O:27])[C@H:11]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[NH:12]C(OC(C)(C)C)=O)[CH3:2].[ClH:30].C(OCC)(=O)C>C(OCC)(=O)C.C(OCC)C>[ClH:30].[CH2:1]([O:3][C:4](=[O:29])[CH2:5][NH:6][C:7](=[O:28])[CH2:8][NH:9][C:10](=[O:27])[C@H:11]([CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[NH2:12])[CH3:2]

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

To the solution of thus obtained N-t-butoxycarbonyl-β-cyclohexyl-L-alanyl-glycyl-glycine ethy lester (506.2 mg, 1.22 mmol) in ethyl acetate (1 mL) under ice-cold condition, add 4M hydrogen chloride/ethyl acetate (3.0 mL, 12 mmol) with stirring, and then the reaction mixture was stirred for 4.5 hours at room temperature. Diethylether (12 mL) was added and the mixture was stirred under ice-cold condition, then the precipitate was collected by filtration to obtain hygroscopic crude crystals. The crude crystals were suspended in diethylether (10 mL)and collected by filtration to obtain β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester hydrochloride (370.3 mg) as colorless crystalline powder (yield 86%).

Workup

  1. stirringthe reaction mixture was stirred for 4.5 hours at room temperature
  2. stirringthe mixture was stirred under ice-cold condition
  3. filtrationthe precipitate was collected by filtration
  4. customto obtain hygroscopic crude crystals
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6f31f8301fd74736977c014c3314cb3d
Source dataset
uspto-grants-2012_03
Patent number
US08133864B2

Reaction notes

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