Trifluoroacetic acid → HCID 66705887, compound

HRID 2276370Notes

Reaction equation

HRID 2276370 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C@@H:19]([CH2:20][C@@H:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:26]=2)[CH2:22][CH3:23])[CH2:18][O:17]C1(C)C)=O)(C)(C)C>O.C(#N)C.[OH-].[Na+]>[NH2:15][C@@H:19]([CH2:20][C@@H:21]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:26]=1)[CH2:22][CH3:23])[CH2:18][OH:17]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66705883HCID 66705883, compound

Product 1

HCID 66705887HCID 66705887, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of trifluoroacetic acid (0.07 ml) in water (6 ml) was added dropwise a solution of (S)-4-[(S)-2-(3-benzyloxy-phenoxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (135 mg) in acetonitrile (1 ml). The mixture was heated for 4 h at 80° C. with mechanical shaking. The mixture was then cooled to room temperature and diluted with 1 N aqueous sodium hydroxide solution. The mixture was extracted twice with ethyl acetate and the combined organic phases were dried over sodium sulphate and concentrated in vacuo to give (2S,4S)-2-amino-4-(3-benzyloxy-phenoxy)-hexan-1-ol (94 mg, quant.) as a light yellow viscous oil. MS (ISP): 316.1 ([M+H]+).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. dry with materialthe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f1cb4485dc24b86bd64bdf94d117e17
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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