5-Chlorocarbonylmethyl-1-azabicyclo[3.3.0]octane hydrochloride → N-[2-(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-ylthio)ethyl]-(1-azabicyclo[3.3.0]octan-5-yl)acetamide

HRID 1645938Notes

Reaction equation

HRID 1645938 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH2:7][C:6]1([CH2:10][C:11](Cl)=[O:12])[CH2:5][CH2:4][CH2:3]2.[CH3:14][C:15]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:67])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:66])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:65])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:64])[CH2:38][CH2:39][CH:40]=[C:41]([CH3:63])[CH2:42][CH2:43][CH:44]=[C:45]([CH3:62])[CH2:46][CH2:47][CH:48]=[C:49]([CH3:61])[CH2:50][CH2:51][CH:52]=[C:53]([CH3:60])[CH2:54][CH2:55][CH:56]=[C:57]([CH3:59])[CH3:58])=[CH:16][CH2:17][S:18][CH2:19][CH2:20][NH2:21]>N1C=CC=CC=1>[CH3:14][C:15]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:67])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:66])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:65])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:64])[CH2:38][CH2:39][CH:40]=[C:41]([CH3:63])[CH2:42][CH2:43][CH:44]=[C:45]([CH3:62])[CH2:46][CH2:47][CH:48]=[C:49]([CH3:61])[CH2:50][CH2:51][CH:52]=[C:53]([CH3:60])[CH2:54][CH2:55][CH:56]=[C:57]([CH3:59])[CH3:58])=[CH:16][CH2:17][S:18][CH2:19][CH2:20][NH:21][C:11](=[O:12])[CH2:10][C:6]12[CH2:7][CH2:8][CH2:9][N:2]1[CH2:3][CH2:4][CH2:5]2

Participants

4

Reactant 2

HCID 199217645-Chlorocarbonylmethyl-1-azabicyclo[3.3.0]octane hydrochloride2×HCID 536869482-(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-ylthio)ethylamine

Product 1

HCID 54345510N-[2-(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-ylthio)ethyl]-(1-azabicyclo[3.3.0]octan-5-yl)acetamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

(1-Azabicyclo[3.3.0]octan-5-yl)acetyl chloride hydrochloride (2.00 g, 8.93 mmol) was added to a solution of 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-ylthio)ethylamine (5.00 g, 6.61 mmol, prepared as described in Example 4) in 75 ml of pyridine at the temperature below 20° C. and the solution was stirred at 25° C. for 3 hours. (1-Azabicyclo[3.3.0]octan-5-yl)acetyl chloride hydrochloride (0.9 g, 4.02 mmol) was further added to the reaction mixture at the temperature below 20° C. and the solution was stirred at 25° C. for an hour. The solvent in the reaction mixture was evaporated in vacuo to dryness and the remaining residue was partitioned between chloroform and 10% sodium hydroxide aqueous solution. The organic layer was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to dryness to give a brown residue. The residue was chromatographed on silica gel, eluting with CH2Cl2 /MeOH (10:0-10:1.5) to afford 5.2 g (86.7%) of the desired compound, as a colorless oil.

Workup

  1. stirringthe solution was stirred at 25° C. for an hour
  2. customThe solvent in the reaction mixture was evaporated in vacuo to dryness
  3. customthe remaining residue was partitioned between chloroform and 10% sodium hydroxide aqueous solution
  4. washThe organic layer was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to dryness
  8. customto give a brown residue
  9. customThe residue was chromatographed on silica gel
  10. washeluting with CH2Cl2 /MeOH (10:0-10:1.5)

Sources & evidence

ORD record
ord-98d5cb08ae75461fa0d26539538683f3
Source dataset
uspto-grants-1993_01
Patent number
US05177102

Reaction notes

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