Water → HCID 57672057, compound

HRID 1692110Notes

Reaction equation

HRID 1692110 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([N:40]3[CH2:45][CH2:44][C:43]([F:47])([F:46])[CH2:42][CH2:41]3)=[O:39])=[CH:34][CH:33]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][Si](C(C)C)(C(C)C)C(C)C)[CH2:16][CH2:15]2)[C:10]1=[O:31].O.C(O)(C(F)(F)F)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([N:40]3[CH2:45][CH2:44][C:43]([F:47])([F:46])[CH2:42][CH2:41]3)=[O:39])=[CH:34][CH:33]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)[C:10]1=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 66904863HCID 66904863, compound

Product 1

HCID 57672057HCID 57672057, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-3-[3-chloro-4′-(4,4-difluoro-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one (0.15 g) in THF (3 mL), add water (3 mL) and TFA 1 mL). Stir the mixture at room temperature for 5 hours. Partition the reaction with ethyl acetate and sodium bicarbonate (sat. solution), separate the organic layer, extract the aqueous with ethyl acetate again, combine the organic solutions, dry over sodium sulfate, filter and concentrate. Purify the residue on silica gel column with ethyl acetate for 30 minutes and then switch to 8% methanol in dichloromethane to afford 0.06 grams (52%) of the desired product as white solid. MS (m/z): 532 (M+).

Workup

  1. customPartition
  2. customthe reaction with ethyl acetate and sodium bicarbonate (sat. solution)
  3. customseparate the organic layer
  4. extractionextract the aqueous with ethyl acetate again
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the residue on silica gel column with ethyl acetate for 30 minutes

Sources & evidence

ORD record
ord-4f8482f331a34e23a1a1cf2776ce5963
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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