Triethylamine → 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N-tricyclo[3.3.1.13,7]dec-2-yl propanamide

HRID 1614536Notes

Reaction equation

HRID 1614536 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]([C:12]1[CH:17]=[C:16]([SH:18])[CH:15]=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]=1[OH:23])([CH3:11])[CH3:10].[CH:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH:25]1[NH:34][C:35](=[O:38])[CH:36]=[CH2:37])[CH2:31]2>CO>[CH3:11][C:9]([C:12]1[CH:17]=[C:16]([S:18][CH2:37][CH2:36][C:35]([NH:34][CH:25]2[CH:26]3[CH2:32][CH:30]4[CH2:29][CH:28]([CH2:33][CH:24]2[CH2:31]4)[CH2:27]3)=[O:38])[CH:15]=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]=1[OH:23])([CH3:8])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 14986569N-(adamantan-2-yl)prop-2-enamide

Product 1

HCID 149865703-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N-tricyclo[3.3.1.13,7]dec-2-yl propanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the procedure of Example 4, triethylamine (0.5 ml) was added to a solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (1.19g, 0.005 mole) and the N-tricyclo[3.3.1.13,7 ]dec-2-yl-2-propenamide (1.02 g, 0.005 mole) in methanol (100 ml) and the solution stirred ar room temperature for 12 hours. The solvent and triethylamine were removed on a rotary evaporator and the product purified by chromatography on silica, recrystallized from ethyl acetate/ethyl ether/hexane and dried, m.p. ca. 155.5°-156° C. Analysis calc. for C27H41NO2S(443.69):

Workup

  1. customThe solvent and triethylamine were removed on a rotary evaporator
  2. customthe product purified by chromatography on silica
  3. customrecrystallized from ethyl acetate/ethyl ether/hexane
  4. customdried

Sources & evidence

ORD record
ord-d64aeb90460b409584f800836cf4477d
Source dataset
uspto-grants-1993_03
Patent number
US05198435

Reaction notes

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