Water → HCID 67266313, compound

HRID 1971313Notes

Reaction equation

HRID 1971313 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]([NH:13][C@@H:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:16]([C:27]4[N:31]([CH2:32][CH2:33][O:34]S(C)(=O)=O)[C:30]5[CH:39]=[CH:40][CH:41]=[CH:42][C:29]=5[N:28]=4)[CH2:15]3)=[O:12])[CH:9]=[CH:10][C:2]1=2.[C:43]([O-])([O-])=O.[K+].[K+].O.[C:50]([O:53][CH2:54][CH3:55])(=O)[CH3:51]>C(O)(C(F)(F)F)=O>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]([NH:13][C@@H:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:16]([C:27]4[N:31]([CH2:32][CH2:33][O:34][CH:54]5[CH2:55][CH2:43][CH2:51][CH2:50][O:53]5)[C:30]5[CH:39]=[CH:40][CH:41]=[CH:42][C:29]=5[N:28]=4)[CH2:15]3)=[O:12])[CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86625965HCID 86625965, compound

Product 1

HCID 67266313HCID 67266313, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(2R,4R)-tert-butyl 4-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-2-(1-(2-(methylsulfonyloxy)ethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate (65 mg, 0.11 mmol) was dissolved in TFA (1 mL) and stirred at room temperature for 2 hours. The reaction mixture was concentrated to removed TFA, the residue was dissolved in DMF (1 mL) and K2CO3 (30 mg, 0.22 mmol) was added to it, the resulting mixture was stirred at 60° C. for over night. Water and ethyl acetate were added to reaction mixture, the organic layer was separated and dried over MgSO4 and concentrated. Purification was done by Companion (ReadSep, 12 g, silica gel packed) with CH3OH/CH2Cl2 from 1-5% to give a white solid 30 mg (60%) as title compound. LC-MS: 405.2 (t=1.4 min).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto removed TFA
  3. dissolutionthe residue was dissolved in DMF (1 mL)
  4. stirringthe resulting mixture was stirred at 60° C. for over night
  5. customthe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customPurification

Sources & evidence

ORD record
ord-d3d49717e13148b5997fb2823b2e88c0
Source dataset
uspto-grants-2013_04
Patent number
US08431597B2

Reaction notes

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