Hydrochloric Acid → (2R,3R,4S)-2-Amino-3-benzyloxy-4-dibenzylamino-5-(3,5-difluorophenyl)-pentan-1-ol

HRID 20342Notes

Reaction equation

HRID 20342 reaction equation
C(OC([N:8]1[CH:12]([C@@H:13]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@@H:14]([N:24]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:15][C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C@@H:12]([C@@H:13]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C@@H:14]([N:24]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=1)[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68558042HCID 68558042, compound

Product 1

HCID 68559619(2R,3R,4S)-2-Amino-3-benzyloxy-4-dibenzylamino-5-(3,5-difluorophenyl)-pentan-1-olYield 114.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Dissolve 4-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (2.42 g, 3.68 mmol) in dry dioxane (16 mL). To the solution add 4 M hydrogen chloride in 1,4-dioxane (32.2 mL, 129 mmol) and stir for three hours. Concentrate to give the hydrochloride salt of the desired product as a white solid (2.17 g, 100%). Slurry the solid in ethyl acetate (150 mL) and stir vigorously with saturated sodium bicarbonate (100 mL). Separate the layers and dry (magnesium sulfate) to give the desired compound.

Workup

  1. concentrationConcentrate

Sources & evidence

ORD record
ord-4d3283fa1b374872a9e9cf9ddcd6b3ef
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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