Chloroform → HCID 68433470, compound

HRID 2192871Notes

Reaction equation

HRID 2192871 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:45][CH:46]([CH3:48])[CH3:47])[C@H:20]2[CH2:25][C@@H:24]([C:26]([N:28]3[CH2:33][CH2:32][CH:31]([C:34]([OH:37])([CH3:36])[CH3:35])[CH2:30][CH2:29]3)=[O:27])[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C(Cl)(Cl)[Cl:57]>>[ClH:57].[ClH:57].[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([C@H:20]2[CH2:25][C@@H:24]([C:26]([N:28]3[CH2:29][CH2:30][CH:31]([C:34]([OH:37])([CH3:35])[CH3:36])[CH2:32][CH2:33]3)=[O:27])[CH2:23][NH:22][CH2:21]2)[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:18])=[CH:7][N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 59625244HCID 59625244, compound

Product 1

HCID 68433470HCID 68433470, compound

Procedure

tert-Butyl (3S,5R)-3-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-{[4-(1-hydroxy-1-methylethyl)piperidin-1-yl]carbonyl}piperidine-1-carboxylate (120 mg) was dissolved in chloroform (3 ml), TFA (1 ml) was added and the mixture was stirred for 1 hr. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate, washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in methanol (2 ml), hydrochloric acid-methanol (2 ml) was added, and the solvent was evaporated under reduced pressure to give the object compound (66 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in methanol (2 ml)
  7. additionhydrochloric acid-methanol (2 ml) was added
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6d74126eeba640a69c90b8b5e3bda0f7
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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