Hydrochloric Acid → 2,6-Dimethyl-L-tyrosyl-N-[(2R)-2-amino-3-phenylpropyl]-D-alaninamide

HRID 1849990Notes

Reaction equation

HRID 1849990 reaction equation
C(OC([NH:8][C@H:9]([C:20]([NH:22][C@@H:23]([C:25]([NH:27][CH2:28][C@H:29]([NH2:37])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:26])[CH3:24])=[O:21])[CH2:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=1[CH3:19])=O)(C)(C)C.Cl>O1CCOCC1>[CH3:19][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[CH2:10][C@@H:9]([C:20]([NH:22][C@@H:23]([C:25]([NH:27][CH2:28][C@H:29]([NH2:37])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:26])[CH3:24])=[O:21])[NH2:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71229909N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-amino-3-phenylpropyl}-D-alaninamide

Product 1

HCID 712299072,6-Dimethyl-L-tyrosyl-N-[(2R)-2-amino-3-phenylpropyl]-D-alaninamideYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-amino-3-phenylpropyl}-D-alaninamide (203 mg, 0.36 mmol) was dissolved in 1 mL dioxane and hydrogen chloride (4M solution in dioxane, 1 mL, 4 mmol) added and the mixture stirred at room temperature for 16 h. The mixture was evaporated under reduced pressure and the residue purified by preparative HPLC and then freeze dried to provide the title compound (83 mg, 56%) as a white solid.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue purified by preparative HPLC
  3. customfreeze dried

Sources & evidence

ORD record
ord-aa6ae07089374649a4b4dce49aee91cf
Source dataset
uspto-grants-2015_02
Patent number
US08957025B2

Reaction notes

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