Hydrochloric Acid → methyl N-(3-amino-2-methylpropyl)-N-[(benzyloxy)carbonyl]-D-alaninate

HRID 854280Notes

Reaction equation

HRID 854280 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:18][CH:19]([CH3:29])[CH2:20][NH:21]C(OC(C)(C)C)=O)[C@@H:12]([C:14]([O:16][CH3:17])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[NH2:21][CH2:20][CH:19]([CH3:29])[CH2:18][N:11]([C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C@@H:12]([C:14]([O:16][CH3:17])=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69154997Methyl N-[(benzyloxy)carbonyl]-N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate

Product 1

HCID 69155205methyl N-(3-amino-2-methylpropyl)-N-[(benzyloxy)carbonyl]-D-alaninate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl N-[(benzyloxy)carbonyl]-N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate (1.6 g, 3.9 mmol) was treated with 4N hydrogen chloride in dioxane (10 mL) at room temperature for 2 hr. The solvent was removed under a stream of nitrogen, and the crude product was purified by flash chromatography on a Biotage® system (silica, 7% pre-mixed 2N ammonia/methanol in dichloromethane) to yield methyl N-(3-amino-2-methylpropyl)-N-[(benzyloxy)carbonyl]-D-alaninate as colorless viscous oil. MS (M+1): 309.4

Workup

  1. customThe solvent was removed under a stream of nitrogen
  2. customthe crude product was purified by flash chromatography on a Biotage® system (silica, 7% pre-mixed 2N ammonia/methanol in dichloromethane)

Sources & evidence

ORD record
ord-61a24e7873d6497484f55359e6c29787
Source dataset
uspto-grants-2007_08
Patent number
US07259160B2

Reaction notes

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