Hydrochloric Acid → 1-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride

HRID 660422Notes

Reaction equation

HRID 660422 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[N:10]([CH2:15][CH:16]([OH:33])[CH:17]([NH:25]C(OC(C)(C)C)=O)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:11][CH:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:35]>CO.C(O)(C)C>[Cl-:35].[CH2:18]([CH:17]([NH3+:25])[CH:16]([OH:33])[CH2:15][N:10]([C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:34])[CH2:11][CH:12]([CH3:14])[CH3:13])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66769801HCID 66769801, compound

Product 1

HCID 685086951-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

(3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-isobutyl-carbamic acid benzyl ester (3) (34.30 g, 72.90 mmol, 1 equiv) was dissolved in methanol (170 mL), followed by the addition of 5-6 N HCl in isopropanol (75 mL). The solution was stirred at room temperature for 64 h. Volatiles were evaporated under reduced pressure. The crude product was coevaporated with ethyl acetate (150 mL) to obtain 4 as a white solid (29.70 g, 72.90 mmol, quantitative). LRMS (ES+): m/z 371 [M+H]+.

Workup

  1. customVolatiles were evaporated under reduced pressure

Sources & evidence

ORD record
ord-e93b13133c3a4429ac41a1b20cfa7475
Source dataset
uspto-grants-2011_12
Patent number
US08084494B2

Reaction notes

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