Hydrochloric Acid → HCID 70444605, compound

HRID 542647Notes

Reaction equation

HRID 542647 reaction equation
[CH3:1][N:2]([CH3:32])[CH2:3][C@H:4]([C:13]([NH:15][C@H:16]([C:24]([NH:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])[NH:5]C(OC(C)(C)C)=O.[ClH:33]>C(O)(=O)C.C(O)C>[ClH:33].[ClH:33].[CH3:32][N:2]([CH3:1])[CH2:3][C@H:4]([C:13]([NH:15][C@H:16]([C:24]([NH:26][CH2:27][CH2:28][CH:29]([CH3:30])[CH3:31])=[O:25])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:14])[NH2:5]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86741422HCID 86741422, compound

Product 1

HCID 70444605HCID 70444605, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of [3-dimethylamino-N2 -(t-butoxycarbonyl)-D-alanyl]-N-(3-methylbutyl)-L-phenylalaninamide (1.84 g.) in acetic acid saturated with hydrogen chloride (50 ml.) was stirred for one and one half hours at room temperature, then stripped of volatiles under vacuum. A solution of the residue (1.87 g.) in ethyl acetate was washed with saturated aqueous sodium bicarbonate, then saturated aqueous sodium chloride, and filtered. Hydrogen chloride (8.2 millimoles) in ethanol was added and the solution was stripped of volatiles, affording (3-dimethylamino-D-alanyl)-N-(3-methylbutyl)-L-phenylalaninamide dihydrochloride as a gum.

Workup

  1. washA solution of the residue (1.87 g.) in ethyl acetate was washed with saturated aqueous sodium bicarbonate
  2. filtrationsaturated aqueous sodium chloride, and filtered

Sources & evidence

ORD record
ord-10a597b126124c57a7e930b4115852a8
Source dataset
uspto-grants-1987_04
Patent number
US04658013

Reaction notes

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