HCID 118045363, compound → HCID 118046368, compound

HRID 595978Notes

Reaction equation

HRID 595978 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][O:13]C(C)(C)[N:11]2C(OC(C)(C)C)=O)[CH:5]=[C:6]([S:8][CH3:9])[CH:7]=1>Cl.O1CCOCC1>[NH2:11][C@@H:10]([C:4]1[CH:5]=[C:6]([S:8][CH3:9])[CH:7]=[C:2]([F:1])[CH:3]=1)[CH2:14][OH:13]

Participants

4

Reactant 1

HCID 118045363HCID 118045363, compound

Product 1

HCID 118046368HCID 118046368, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of (S)-tert-butyl 4-(3-fluoro-5-(methylthio)phenyl)-2,2-dimethyloxazolidine-3-carboxylate (278 mg, 0.814 mmol) in 4 M HCl in dioxane (2.4 mL) was heated to 80° C. overnight. There was still some starting material left. More 4 M HCl in dioxane (2.035 mL, 8.14 mmol) was added, and heated at 80° C. for another 10 h. Solvent was removed under reduced vacuum to provide (S)-2-amino-2-(3-fluoro-5-(methylthio)phenyl)ethanol (194 mg, 0.814 mmol, 100%). LCMS (m/z): 170.1 (MH+-56), 0.26 min.

Workup

  1. waitleft
  2. customSolvent was removed under reduced vacuum

Sources & evidence

ORD record
ord-ce53fde8181846149881b16feb08ab5b
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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