Dichloromethane → HCID 86643145, compound

HRID 1094762Notes

Reaction equation

HRID 1094762 reaction equation
[CH3:1][C:2]1([CH3:21])[N:6]([C:7](=[O:17])[CH2:8][NH:9]C(=O)OC(C)(C)C)[C@@H:5]([CH2:18][CH:19]=[CH2:20])[CH2:4][O:3]1.C(Cl)Cl.[F:25][C:26]([F:36])([F:35])[S:27]([O:30][Si](C)(C)C)(=[O:29])=[O:28]>>[F:25][C:26]([F:36])([F:35])[S:27]([OH:30])(=[O:29])=[O:28].[CH3:1][C:2]1([CH3:21])[N:6]([C:7](=[O:17])[CH2:8][NH2:9])[C@@H:5]([CH2:18][CH:19]=[CH2:20])[CH2:4][O:3]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 65367Trimethylsilyl triflateHCID 59396014HCID 59396014, compound

Product 1

HCID 86643145HCID 86643145, compound

Procedure

To a solution of 1,1-dimethylethyl {2-[(4S)-2,2-dimethyl-4-(2-propen-1-yl)-1,3-oxazolidin-3-yl]-2-oxoethyl}carbamate D22 (28.67 g) in DCM (300 ml) 2,6-dimethylpyridine (27.9 ml, 240 mmol) was added followed by trimethylsilyl trifluoromethanesulfonate (34.7 ml, 192 mmol) the mixture was stirred at room temperature for 30 min. The reaction was quenched with 2 ml of water and the solvent was removed under reduced pressure, the residue was charged on a Biotage 75 L column eluting with [DCM/MeOH 100:0 then 98:2 then 96:4 then 85:15]. Evaporation of the solvent gave: the title compound D23 (21 g). UPLC (Acid FINAL_QC): rt=0.36 minutes, peak observed: 199 (M+1−CHF3O3S)C10H18N2O2.CHF3O3S requires 348. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (s, 3 H), 1.50 (s, 3 H), 2.17-2.43 1.40 (m, 2 H), 3.68-3.98 (m, 4 H), 3.99-4.09 (m, 1 H), 4.83-5.40 (m, 2 H), 5.58-5.97 (m, 1H), 7.63-8.36 (br.s., 2 H)

Workup

  1. customThe reaction was quenched with 2 ml of water
  2. customthe solvent was removed under reduced pressure
  3. additionthe residue was charged on a Biotage 75 L column
  4. washeluting with [DCM/MeOH 100:0
  5. customEvaporation of the solvent
  6. customgave

Sources & evidence

ORD record
ord-a74197d466134f8fb02b23d0436c7b72
Source dataset
uspto-grants-2012_03
Patent number
US08133908B2

Reaction notes

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