Hydrochloric Acid → (1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl-ammonium chloride

HRID 1432336Notes

Reaction equation

HRID 1432336 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:23]=1)[C@@H:9]([OH:20])[CH2:10][C@H:11]([C:13](=[O:19])[NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH3:12])(C)(C)C.[ClH:37]>O1CCOCC1>[Cl-:37].[CH2:29]([O:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][C@H:8]([NH3+:7])[C@@H:9]([OH:20])[CH2:10][C@H:11]([C:13](=[O:19])[NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH3:12])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11648991[(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-carbamic acid tert-butyl ester

Product 1

HCID 86612512(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl-ammonium chloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-carbamic acid tert-butyl ester (660 mg, 1.3 mmol) is dissolved in 4M HCl in dioxane (14 ml) and stirred at rt for 75 min. Evaporation of the solvent and washing the residue with diethyl ether gives a white foam (535 mg).

Workup

  1. customEvaporation of the solvent
  2. washwashing the residue with diethyl ether

Sources & evidence

ORD record
ord-1fd598161b924e2baf87aa08e53ab8b1
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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