Water → 4-(2-(1,2-dihydroxyethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

HRID 528652Notes

Reaction equation

HRID 528652 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][N:8]([C:30]2[S:31][CH:32]=[CH:33][N:34]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH:27]=[CH2:28])[CH2:19][CH2:18][O:17][C:16]=3[CH:29]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C[N+]1([O-])CC[O:41]CC1.[OH2:45]>CC(O)(C)C.O=[Os](=O)(=O)=O>[OH:45][CH:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:20]1[CH2:19][CH2:18][O:17][C:16]2[CH:29]=[C:12]([S:9]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:36][CH:35]=3)[C:30]3[S:31][CH:32]=[CH:33][N:34]=3)(=[O:11])=[O:10])[CH:13]=[CH:14][C:15]1=2)[CH2:28][OH:41]

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 89761662N-(4-methoxybenzyl)-N-(thiazol-2-yl)-4-(2-vinylphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Product 1

HCID 897617304-(2-(1,2-dihydroxyethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamideYield 37.5%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

To a solution of N-(4-methoxybenzyl)-N-(thiazol-2-yl)-4-(2-vinylphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (750 mg, 1.445 mmol) in t-BuOH (10 mL) and water (5 mL) was added NMO (338 mg, 2.890 mmol, Aldrich) followed by OsO4 (4% in water) (0.7 mL, 0.144 mmol, Aldrich) at 0° C. The reaction mixture was stirred at ambient temperature for 12 h. After completion, the reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 mL) and extracted with DCM (2×10 mL). The organic layer was dried over sodium sulfate and concentrated reduced pressure to obtain crude 4-(2-(1,2-dihydroxyethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (300 mg, 37.5%) which was used in the next step without purification. m/z (ESI) 553.9 (M+H)+.

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 mL)
  2. extractionextracted with DCM (2×10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated reduced pressure

Sources & evidence

ORD record
ord-7448a4e7113a4e87bddcb535589ecf4f
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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