Hydrochloric Acid → (1-(2-Aminoacetyl)-4-(3-fluoro-2-methylbenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate

HRID 655972Notes

Reaction equation

HRID 655972 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:42])[O:11][CH2:12][C:13]2([C:30](=[O:41])[NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=3[CH3:40])[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>C(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:42])[O:11][CH2:12][C:13]2([C:30](=[O:41])[NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=3[CH3:40])[CH2:14][CH2:15][N:16]([C:19](=[O:29])[CH2:20][NH2:21])[CH2:17][CH2:18]2)=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59778453(1-(2-(Tert-butoxycarbonylamino)acetyl)-4-(3-fluoro-2-methylbenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate

Product 1

HCID 59778445(1-(2-Aminoacetyl)-4-(3-fluoro-2-methylbenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of give (1-(2-(tert-butoxycarbonylamino)acetyl)-4-(3-fluoro-2-methylbenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate (12 mg, 0.021 mmol, 1.0 equiv.) in CH2Cl2 (1 mL) was added 4N HCl (1 mL). The mixture was stirred at rt for about 1 h and concentrated to dryness. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give (1-(2-aminoacetyl)-4-(3-fluoro-2-methylbenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate (8 mg, 79%). LRMS (M+H+) m/z 485.1.

Workup

  1. concentrationconcentrated to dryness
  2. customThe resulting residue was purified on RP-HPLC
  3. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-7a41c48bbe5f42e4a3b2195413563e96
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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