Pyridine → (4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-((methylsulfonyloxy)methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylate

HRID 1500285Notes

Reaction equation

HRID 1500285 reaction equation
[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:18][N:17]=[C:16]([CH2:19][OH:20])[CH:15]=3)=[CH:10][CH:9]=2)[O:6][C:5]([CH3:22])([CH3:21])[N:4]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].N1C=CC=CC=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:18][N:17]=[C:16]([CH2:19][O:20][S:37]([CH3:36])(=[O:39])=[O:38])[CH:15]=3)=[CH:10][CH:9]=2)[O:6][C:5]([CH3:22])([CH3:21])[N:4]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 58631212HCID 58631212, compound

Product 1

HCID 86695496(4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-((methylsulfonyloxy)methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4S,5R)-tert-butyl 4-(fluoromethyl)-5-(4-(3-(hydroxymethyl)isoxazol-5-yl)phenyl)-2,2-dimethyloxazolidine-3-carboxylate (see US2004/0082553, page 67 (page 68 of pdf version)) (1000 mg, 2.45 mmol) in CH2Cl2 (25 mL) at 5° C. is treated with pyridine (0.23 mL, 2.95 mmol) and methanesulfonylchloride (0.19 mL, 2.45 mmol) then stirred for 1 hour, washed with saturated aqueous sodium bicarbonate, concentrated and used as is (1130 mg). m/z (Cl) 485 [M+H].

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-fb4308ff0e1743d9ae6a279a4326b040
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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