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Acetic Acid → {[(3S,4R)-4-(4-chlorophenyl)-1-cyclopropylpyrrolidine-3-yl]carbonyl}-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide HCl salt

HRID 1361338
Notes
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Reaction equation

HRID 1361338 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][NH:11][CH2:10][C@H:9]2[C:13]([N:15]2[CH2:24][C@@H:23]([N:25]([CH:32]3[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH2:33]3)[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:22][C@H:16]2[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[O:14])=[CH:4][CH:3]=1.C(O[C:43]1(O[Si](C)(C)C)[CH2:45][CH2:44]1)C.[Na].C([BH3-])#N.C(O)(=O)C>ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11]([CH:43]3[CH2:45][CH2:44]3)[CH2:10][C@H:9]2[C:13]([N:15]2[CH2:24][CH:23]([N:25]([CH:32]3[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH2:33]3)[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:22][C@H:16]2[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[O:14])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 24826348(4S)-1-[(3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-yl]carbonyl-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamideHCID 131717404HCID 131717404, compound

Product 1

HCID 86636656
{[(3S,4R)-4-(4-chlorophenyl)-1-cyclopropylpyrrolidine-3-yl]carbonyl}-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide HCl salt

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (4S)-1-[(3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-yl]carbonyl-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide (100 mg, 0.18 mmol) prepared in Example E1-1 in DCE (5 ml) was added 1-ethoxycyclopropoxytrimethylsilane (47 mg, 0.27 mmol) and sodium-cyanoborohydride (23 mg, 0.36 mmol), added a catalytic amount of acetic acid, and the solution was stirred at 80° C. for 2 h. After the reaction finished, the solvent was concentrated in vacuo, and extracted with a saturated NaHCO3 aqueous solution and EtOAc. The organic solution was dried over MgSO4, concentrated in vacuo, and the residue was purified by HPLC. This TFA salt of the compound was treated according to the procedure described in Step G of Example A1 to give the title compound.

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. extractionextracted with a saturated NaHCO3 aqueous solution and EtOAc
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by HPLC
  6. additionThis TFA salt of the compound was treated

Sources & evidence

ORD record
ord-f4a740d2771640f2a02dd3b7ac9df09c
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879852B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes