Water → HCID 57672052, compound

HRID 1692104Notes

Reaction equation

HRID 1692104 reaction equation
O.C(O)(C(F)(F)F)=O.[Cl:9][C:10]1[CH:11]=[C:12]([CH:23]=[C:24]([Cl:50])[C:25]=1[CH2:26][C@@H:27]1[CH2:31][CH2:30][N:29]([N:32]2[CH2:37][CH2:36][CH:35]([O:38][Si](C(C)C)(C(C)C)C(C)C)[CH2:34][CH2:33]2)[C:28]1=[O:49])[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=1.C(OCC)(=O)C>C1COCC1>[Cl:9][C:10]1[CH:11]=[C:12]([CH:23]=[C:24]([Cl:50])[C:25]=1[CH2:26][C@@H:27]1[CH2:31][CH2:30][N:29]([N:32]2[CH2:37][CH2:36][CH:35]([OH:38])[CH2:34][CH2:33]2)[C:28]1=[O:49])[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 66904916HCID 66904916, compound

Product 1

HCID 57672052HCID 57672052, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add water (6 mL) and TFA (2 mL) to (R)-4-{3,5-dichloro-4-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-phenoxy}-benzamide (0.21 g) in THF (6 mL). Stir the mixture at room temperature for 12 hours. Dilute the reaction with ethyl acetate and wash with sodium bicarbonate (sat. solution), separate the organic layer, dry over sodium sulfate, filter and concentrate. Purify the residue on silica gel column by using ethyl acetate first, then switch to 5% methanol in dichloromethane to afford 0.158 g (100%) of the desired product as white solid. MS (m/z): 478 (M+).

Workup

  1. additionDilute
  2. washwash with sodium bicarbonate (sat. solution)
  3. customseparate the organic layer
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue on silica gel column

Sources & evidence

ORD record
ord-903f25c109134a4f8e4d3db52255f098
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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