Methanol → HCID 53754927, compound

HRID 845157Notes

Reaction equation

HRID 845157 reaction equation
C(N([CH2:6][CH3:7])CC)C.C(S)CCS.[CH:13]1([CH:19]([OH:32])[C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH2:22][N:23](C)C)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-:33].[Na+].[CH3:35][OH:36]>O>[NH2:23][CH2:22][CH:21]=[C:20]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:32][C:35]([O:36][CH2:6][CH3:7])=[O:33]

Participants

7

Reactant 5

HCID 887MethanolHCID 80131,3-PropanedithiolHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 538458471-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

Product 1

HCID 53754927HCID 53754927, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (1.05 cc) and 1,3-propanedithiol (0.74 cc) are added to a solution of 4-azido-1,2-diphenyl-1-ethoxycarbonyloxy-2-butene (Z) (0.5 g) in methanol (7.5 cc). The mixture is stirred under a nitrogen atmosphere for 18 hours at ambient temperature. The reaction mixture is then poured into water (10 cc), adjusted to pH 12 with an aqueous solution of 4N sodium hydroxide and then extracted 3 times with methylene chloride. The organic phase is dried over magnesium sulphate, filtered and then evaporated under reduced pressure (2.7 kPa) at 30° C. The residue obtained is purified by chromatography on silica gel [eluent: ethyl acetate/methanol (40/60 by volume)], 5 cc fractions being collected. Fractions 15 to 25 are evaporated to dryness under reduced pressure (2.7 kPa) at 30° C. In this way 1-amino-3,4-diphenyl-4-ethoxycarbonyloxy-2-butene (E) (0.168 g) is obtained in the form of a pale yellow oil [R f =0.15, eluent: methanol/ethyl acetate (60/40 by volume)].

Workup

  1. extractionextracted 3 times with methylene chloride
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure (2.7 kPa) at 30° C
  5. customThe residue obtained
  6. customis purified by chromatography on silica gel [eluent: ethyl acetate/methanol (40/60 by volume)], 5 cc fractions
  7. custombeing collected
  8. customFractions 15 to 25 are evaporated to dryness under reduced pressure (2.7 kPa) at 30° C

Sources & evidence

ORD record
ord-b35db2724f32423e8d2d444e8f6d15d7
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

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