HCID 68287924, compound → HCID 178431694, compound

HRID 339871Notes

Reaction equation

HRID 339871 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:20])[C:13]([CH3:15])([CH3:14])[O:12][C:11](OC)=[N:10][S:9]2(=[O:19])=[O:18])[CH:5]=[CH:6][CH:7]=1.[Si:21]([O:28][CH2:29][CH2:30][C@H:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:20])[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:38][C@H:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:30][CH2:29][O:28][Si:21]([C:24]([CH3:27])([CH3:25])[CH3:26])([CH3:23])[CH3:22])=[N:10][S:9]2(=[O:19])=[O:18])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 68287924HCID 68287924, compoundHCID 683591715-(3-Bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Product 1

HCID 178431694HCID 178431694, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 209 mg of 5-(3-bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 181 mg of (S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropylamine in 5 ml of methylene chloride was stirred at room temperature for 1 hour and the conversion was checked by LCMS. Since no conversion had taken place yet, the solvent was concentrated by rotary evaporation and the residue was stirred at room temperature for 19 hours. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (237 mg) with a molecular weight of 595.7 g/mol (C27H39BrN2O4SSi); MS (ESI): m/e=596 (M+h+).

Workup

  1. concentrationthe solvent was concentrated by rotary evaporation
  2. customThe crude product was purified by means of normal phase chromatography
  3. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-de8bf3986a01459e90fe030bc7750ee0
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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