Trifluoroacetic acid → (R)-4-((R)-1-hydroxyethyl)-3-(4-methoxybenzyl)oxazolidin-2-one

HRID 57505Notes

Reaction equation

HRID 57505 reaction equation
C([O:5][C@@H:6]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:5][C@@H:6]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90422856HCID 90422856, compound

Product 1

HCID 90423794(R)-4-((R)-1-hydroxyethyl)-3-(4-methoxybenzyl)oxazolidin-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(4-methoxybenzyl)oxazolidin-2-one (5.90 g, 19.2 mmol) in CH2Cl2 (40 mL) was treated with TFA (40 mL) at room temperature for min. The reaction mixture was concentrated in vacuo, then diluted with CH2Cl2 (˜50 mL), and again concentrated. This procedure was repeated three times to remove TFA. Flash column chromatography (EtOAc/Heptane 30-100%) gave 3.81 g (R)-4-((R)-1-hydroxyethyl)-3-(4-methoxybenzyl)oxazolidin-2-one. 1H NMR (400 MHz, MeOD) δ 7.31-7.21 (m, 2H), 7.00-6.87 (m, 2H), 4.67 (d, J=15.0 Hz, 1H), 4.34-4.18 (m, 3H), 3.95 (q, J=6.2 Hz, 1H), 3.80 (s, 3H), 3.68 (dt, J=8.7, 5.5 Hz, 1H), 1.09 (d, J=6.4 Hz, 3H). MS m/z 252.2 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with CH2Cl2 (˜50 mL)
  3. concentrationagain concentrated
  4. customto remove TFA

Sources & evidence

ORD record
ord-27a4a4e30f8d4b92b8ee5950225570e6
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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