Acetic Acid → HCID 68785177, compound

HRID 1808130Notes

Reaction equation

HRID 1808130 reaction equation
[ClH:1].[NH2:2][CH:3]([C:14]([NH2:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.C([O-])(O)=O.[Na+].[CH3:22][N:23]([CH3:37])[C:24]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1.C(O)(=O)C.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>O1CCCC1.ClCCCl>[ClH:1].[ClH:1].[CH3:22][N:23]([CH3:37])[C:24]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:25][CH2:26][CH:27]([NH:2][CH:3]([CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)[C:14]([NH2:16])=[O:15])[CH2:28][CH2:29]1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 24436Sodium SulfateHCID 17877795373-47-0HCID 516892Sodium Bicarbonate2×HCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 68785177HCID 68785177, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

D,L-tryptophanamide hydrochloride (1.49 g, 6.25 mmol) was vigorously stirred with 1,2-dichloroethane (30 ml), tetrahydrofuran (20 ml) and saturated NaHCO3 solution (40 ml) for 15 min and the aqueous phase was then immediately extracted with a tetrahydrofuran/ethyl acetate mixture (1:3.5×40 ml). After drying with Na2SO4 the organic phase was concentrated to low volume. The released base (1.03 g, 5.06 mmol) and 4-(dimethylamino)-4-phenylcyclohexanone (1.09 g, 5.06 mmol) were dissolved in tetrahydrofuran (40 ml) and 1,2-dichloroethane (30 ml) in argon. Glacial acetic acid (0.291 ml, 5.06 mmol) and Na2SO4 (2.53 g) were added to the clear solution. After a reaction time of 15 min the reaction mixture was mixed with NaBH(OAc)3 (1.52 g, 7.08 mmol) and stirred for 2 d at room temperature. 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 (150 g) was conducted with ethyl acetate/methanol (1:1).

Workup

  1. extractionthe aqueous phase was then immediately extracted with a tetrahydrofuran/ethyl acetate mixture (1:3.5×40 ml)
  2. dry with materialAfter drying with Na2SO4 the organic phase
  3. concentrationwas concentrated to low volume
  4. stirringstirred for 15 min
  5. extractionThe aqueous phase was extracted with dichloromethane (2×40 ml)
  6. concentrationThe combined organic phases were concentrated to low volume
  7. customafter drying
  8. customa light brown oil was obtained
  9. customThe chromatographic separation of the substance mixture on silica gel 60 (150 g)

Sources & evidence

ORD record
ord-af49b71708b443a1850828329510adf6
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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