Hydrochloric Acid → Benzyl L-phenylalaninate hydrochloride (1:1)

HRID 61301Notes

Reaction equation

HRID 61301 reaction equation
C(OC([NH:8][C@@H:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=O)(C)(C)C.[ClH:27]>C(OCC)C.O1CCOCC1>[ClH:27].[NH2:8][C@@H:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 128332N-tert-butoxycarbonylphenylalanine benzyl ester

Product 1

HCID 12636208Benzyl L-phenylalaninate hydrochloride (1:1)

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzyl (2S)-2-(tert-butoxycarbonylamino)-3-phenyl-propanoate (12.8 g, 36 mmol) was stirred in HCl, 2 M in diethyl ether (90 mL) and HCl, 4 M in dioxane (18 mL) and the resulting mixture was stirred overnight at room temperature. The mixture was then diluted with hexanes (100 mL) and filtered to collect the title compound (7.98 g, 76%) as a fine white powder. 1H NMR (CD3OD, 400 MHz): δ (ppm) 7.40-7.15 (m, 10H), 5.23 (s, 2H), 4.36-4.31 (m, 1H), 3.26-3.12 (m, 2H).

Workup

  1. filtrationfiltered
  2. customto collect the title compound (7.98 g, 76%) as a fine white powder

Sources & evidence

ORD record
ord-26515bd6e10f435c8a6140bf338a67f2
Source dataset
uspto-grants-2016_09
Patent number
US09441012B2

Reaction notes

Loading…