Hydrochloric Acid → (3S)-3-[[5-(3-bromophenyl)-6,6-dimethyl-4,4-dioxo-5H-1,4,3-oxathiazin-2-yl]amino]-3-phenylpropan-1-ol

HRID 339842Notes

Reaction equation

HRID 339842 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:16][C@H:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)=[N:10][S:9]2(=[O:35])=[O:34])[CH:5]=[CH:6][CH:7]=1.Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:16][C@H:17]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:18][CH2:19][OH:20])=[N:10][S:9]2(=[O:35])=[O:34])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178431688HCID 178431688, compound

Product 1

HCID 178431669(3S)-3-[[5-(3-bromophenyl)-6,6-dimethyl-4,4-dioxo-5H-1,4,3-oxathiazin-2-yl]amino]-3-phenylpropan-1-olYield 68.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To detach the protecting group, 70 mg of [5-(3-bromophenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl]-[(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropyl]amine were taken up in 1.5 ml of methanol and, after addition of 0.15 ml of concentrated hydrochloric acid, stirred at room temperature for 1 hour. The reaction solution was concentrated by rotary evaporation and the residue purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined and freed of the solvent under reduced pressure. The residue was dissolved in acetonitrile and lyophilized. This gave the product (38.6 mg) with a molecular weight of 467.4 g/mol (C20H23BrN2O4S); MS (ESI): m/e=468 (M+H+).

Workup

  1. concentrationThe reaction solution was concentrated by rotary evaporation
  2. customthe residue purified in a purification laboratory by means of preparative HPLC
  3. dissolutionThe residue was dissolved in acetonitrile

Sources & evidence

ORD record
ord-3bb9a401807c48ae9cdfbcfbf1e795ef
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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