Methanol → HCID 67025449, compound

HRID 1992299Notes

Reaction equation

HRID 1992299 reaction equation
[OH:1][C:2]([C@H:5]1[S:10][C:9]([NH:11]C(=O)OC(C)(C)C)=[N:8][C@:7]([CH3:31])([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:26]=[N:27][CH:28]=[N:29][CH:30]=3)[CH:20]=2)[CH2:6]1)([CH3:4])[CH3:3].CO.[F:34]C(F)(F)C(O)=O>>[NH2:11][C:9]1[S:10][C@H:5]([C:2]([OH:1])([CH3:4])[CH3:3])[CH2:6][C@:7]([C:19]2[CH:24]=[CH:23][C:22]([F:34])=[C:21]([C:25]3[CH:26]=[N:27][CH:28]=[N:29][CH:30]=3)[CH:20]=2)([CH3:31])[N:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 86635615HCID 86635615, compound

Product 1

HCID 67025449HCID 67025449, compoundYield 67.5%

Procedure

A solution of tert-butyl (4S,6S)-6-(2-hydroxypropan-2-yl)-4-methyl-4-(3-(pyrimidin-5-yl)phenyl)-5,6-dihydro-4H-1,3-thiazin-2-ylcarbamate (221 mg, 0.50 mmol) in trifluoroacetic acid (2 mL) is stirred at room temperature for 80 min. The mixture is added directly to a MeOH-equilibrated SCX column. The column is washed with MeOH (100 mL) and the product is eluted with 7N NH3 in MeOH (100 mL). The solution is concentrated under reduced pressure. The residue is diluted with CH2Cl2 and HCl (g) is bubbled through for 5 min. The reaction mixture is concentrated to give the title compound (67.5% yield): MS (m/z): 343 (M+1).

Workup

  1. washThe column is washed with MeOH (100 mL)
  2. washthe product is eluted with 7N NH3 in MeOH (100 mL)
  3. concentrationThe solution is concentrated under reduced pressure
  4. additionThe residue is diluted with CH2Cl2 and HCl (g)
  5. customis bubbled through for 5 min
  6. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-13a29e0e2c2e4ca1a00274d4f4894840
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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