Hydrochloric Acid → (1-(2-Aminoacetyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate

HRID 655951Notes

Reaction equation

HRID 655951 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:41])[O:11][CH2:12][C:13]2([C:30](=[O:40])[NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])[CH2:18][CH2:17][N:16]([C:19](=[O:29])[CH2:20][NH:21]C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[CH:5][CH:4]=1)[CH3:2].Cl>CO>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:41])[O:11][CH2:12][C:13]2([C:30](=[O:40])[NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])[CH2:18][CH2:17][N:16]([C:19](=[O:29])[CH2:20][NH2:21])[CH2:15][CH2:14]2)=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59778528(1-(2-(Tert-butoxycarbonyl)aminoacetyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate

Product 1

HCID 59778431(1-(2-Aminoacetyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamateYield 110.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1-(2-(tert-butoxycarbonyl)aminoacetyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate (87 mg, 0.15 mmol) in CH3OH (1 mL) was added HCl (4M in dioxane, 100 μL, 0.4 mmol, 2.6 equiv.), which was stirred for 2 h. The reaction mixture was concentrated to dryness by co-evaporating with toluene to give (1-(2-aminoacetyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate (81 mg, quant.). LRMS (M+H+) m/z 487.1.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness by co-evaporating with toluene

Sources & evidence

ORD record
ord-ebe4964d402a44d49972aabc7cbbda4b
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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