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

HRID 1487547
Notes
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Reaction equation

HRID 1487547 reaction equation
[NH2:1][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]3[O:18][C:17]([CH3:20])([CH3:19])[N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:15]3[CH2:28][F:29])=[CH:10][CH:9]=2)[O:5][N:4]=1.[S:30](Cl)([CH3:33])(=[O:32])=[O:31].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[F:29][CH2:28][C@@H:15]1[C@@H:14]([C:11]2[CH:10]=[CH:9][C:8]([C:6]3[O:5][N:4]=[C:3]([CH2:2][NH:1][S:30]([CH3:33])(=[O:32])=[O:31])[CH:7]=3)=[CH:13][CH:12]=2)[O:18][C:17]([CH3:19])([CH3:20])[N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86695497(4S,5R)-tert-butyl 5-(4-(3-(aminomethyl)isoxazol-5-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 86695500(4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-(methylsulfonamido-methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylateYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a methylene chloride (10 ml) solution of (4S,5R)-tert-butyl 5-(4-(3-(aminomethyl)isoxazol-5-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidine-3-carboxylate (270 mg, 0.66 mmol) that had been cooled to 0° C. is added mesyl chloride (83 mg, 0.73 mmol) and diisopropylethylamine (94 mg, 0.73 mmol) sequentially. The reaction is stirred at 0° C. for thirty minutes then quenched with water (2 ml). The quenched reaction is stirred for thirty minutes at room temperature. The organic phase is dried over sodium sulfate and concentrated to give the title compound (310 mg): m/z (CI) 484 ([M+H]+.

Workup

  1. customthen quenched with water (2 ml)
  2. customThe quenched reaction
  3. stirringis stirred for thirty minutes at room temperature
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-25e3cade65224738a765ff45933b522f
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428528B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes