Acetic Acid → HCID 44241901, compound

HRID 1808131Notes

Reaction equation

HRID 1808131 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[NH2:17][C@@H:18]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[C:19]([N:21]([CH3:23])[CH3:22])=[O:20].C(O)(=O)C.[O-]S([O-])(=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>ClCCCl.O1CCCC1>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([NH:17][C@@H:18]([CH2:24][C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)[C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:5][CH2:4]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 10516016HCID 10516016, compoundHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 44241901HCID 44241901, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(dimethylamino)-4-phenylcyclohexanone (1.1 g, 5.41 mmol) was dissolved in a mixture of 1,2-dichloroethane (30 ml) and tetrahydrofuran (40 ml) in argon, mixed with (S)-2-amino-3-(1H-indol-3-yl)-N,N-dimethylpropanamide (1 g, 4.3 mmol), acetic acid (0.31 ml, 5.41 mmol) and Na2SO4 (2.7 g). The mixture was stirred for 15 min at RT and then mixed with sodium triacetoxyboron hydride (1.65 g, 7.57 mmol) and stirred for 48 hours. For work up of the batch the mixture was mixed with saturated NaHCO3 solution (60 ml) and stirred for 15 min. The aqueous phase was extracted with dichloromethane (2×40 ml). The combined organic phases were concentrated to low volume after drying and a light brown oil was obtained. The chromatographic separation of the substance mixture on silica gel 60 (100 g) was conducted with ethyl acetate/methanol (1:1).

Workup

  1. stirringstirred for 48 hours
  2. stirringstirred for 15 min
  3. extractionThe aqueous phase was extracted with dichloromethane (2×40 ml)
  4. concentrationThe combined organic phases were concentrated to low volume
  5. customafter drying
  6. customa light brown oil was obtained
  7. customThe chromatographic separation of the substance mixture on silica gel 60 (100 g)

Sources & evidence

ORD record
ord-64f3f5bc5c43419a8773170d3e2d7c8c
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

Loading…