Hydrogen chloride-ethyl acetate → HCID 57696172, compound

HRID 604248Notes

Reaction equation

HRID 604248 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10](=[O:27])[C@H:11]([CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[NH:12]C(OC(C)(C)C)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[N:1]1([CH2:7][CH2:8][NH:9][C:10](=[O:27])[C@H:11]([CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[NH2:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67038034HCID 67038034, compound

Product 1

HCID 57696172HCID 57696172, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution (0.5 mL) of 233.3 mg of N-t-butoxycarbonyl-β-cyclohexyl-L-alanine 2-(1-piperidinyl)ethyl amide (0.611 mmol) in ethyl acetate, 1.5 mL of 4 M hydrogen chloride/ethyl acetate solution (6 mmol) was added and the reaction mixture was stirred for 4.5 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on alumina [alumina 2.5 g, methanol-chloroform (1:5)], whereby 167.7 mg of the title compound (97%) was obtained as a colorless oil (yield 97%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on alumina [alumina 2.5 g, methanol-chloroform (1:5)]

Sources & evidence

ORD record
ord-12d06e0fda3f4cf5bcdc02cca1468505
Source dataset
uspto-grants-2011_03
Patent number
US07910556B2

Reaction notes

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