Water → HCID 178458230, compound

HRID 339916Notes

Reaction equation

HRID 339916 reaction equation
[Si]([O:8][CH2:9][CH2:10][C@H:11]([NH:19][C:20]1[O:21][C:22]([CH3:38])([CH3:37])[CH:23]([C:28]2[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[CH:30][CH:29]=2)[S:24](=[O:27])(=[O:26])[N:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])(C(C)(C)C)(C)C.[CH3:39][Mg]Br.[Cl-].[NH4+].O>C1COCC1>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C@@H:11]([NH:19][C:20]1[O:21][C:22]([CH3:37])([CH3:38])[CH:23]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([OH:36])([CH3:39])[CH3:35])=[CH:30][CH:29]=2)[S:24](=[O:27])(=[O:26])[N:25]=1)[CH2:10][CH2:9][OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compoundHCID 178466087HCID 178466087, compound

Product 1

HCID 178458230HCID 178458230, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamino]-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-5-yl}phenyl)ethanone (174 mg) in THF (2.5 ml) was added dropwise, at −78° C., a solution of methylmagnesium bromide (1.4 M, 0.44 ml). After 30 min at −78° C., ammonium chloride solution was added to the mixture. After the addition of water, the mixture was extracted with ethyl acetate, dried over magnesium sulfate and concentrated. The residue was dissolved in methanol (2 ml), and 0.2 ml of conc. HCl was added. The resulting mixture was purified in a purification laboratory by means of preparative HPLC. This gave the product (28 mg) with a molecular weight of 464.6 g/mol (C23H29FN2O5S); MS (ESI): m/e=465 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in methanol (2 ml)
  5. addition0.2 ml of conc. HCl was added
  6. customThe resulting mixture was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-b19d4f6394c74ab0bdfc238931a7a842
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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