Triethylamine → HCID 22809833, compound

HRID 2052349Notes

Reaction equation

HRID 2052349 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C@@H:6]2[CH2:30][CH2:29][C@@:28]3([CH3:31])[C@@H:8]([CH2:9][CH2:10][C@@H:11]4[C@@H:27]3[CH2:26][CH2:25][C@@:24]3([CH3:32])[C@H:12]4[CH2:13][CH2:14][C@@H:15]3[C@H:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:7]2)[CH2:3]1.C(N(CC)CC)C.[CH2:40]([S:56](Cl)(=[O:58])=[O:57])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]>C1C=CC=CC=1>[CH2:40]([S:56]([O:1][CH:2]1[CH2:3][N:4]([C@@H:6]2[CH2:30][CH2:29][C@@:28]3([CH3:31])[C@@H:8]([CH2:9][CH2:10][C@@H:11]4[C@@H:27]3[CH2:26][CH2:25][C@@:24]3([CH3:32])[C@H:12]4[CH2:13][CH2:14][C@@H:15]3[C@H:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:7]2)[CH2:5]1)(=[O:58])=[O:57])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 969231-Hexadecanesulfonyl chlorideHCID 705915383-Azetidinol, 1-[(3α,5α)-cholestan-3-yl]-

Product 1

HCID 22809833HCID 22809833, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred suspension of 1.5 g 3α-(3-hydroxy-1-azetidinyl)-5α-cholestane (prepared as described in Example 1 and purified by column chromatography, m.p. 191.5°-195.5° C.) and 0.34 g triethylamine in 33 ml dry benzene, add a solution of 0.78 g 98% hexadecanesulfonyl chloride in 7 ml dry benzene. Stir the resultant cloudy solution at room temperature for 20 days. Concentrate the reaction mixture in vacuo to about one-third the original volume and filter the resultant precipitate. Remove the solvent in vacuo from the filtrate. Dissolve the resultant residue in 80 ml ethyl ether and filter through a column of 45-50 g silica gel eluting with additional ethyl ether as needed to afford the title compound, m.p. 64.5°-68.0° C.

Workup

  1. concentrationConcentrate the reaction mixture in vacuo to about one-third the original volume
  2. filtrationfilter the resultant precipitate
  3. customRemove the solvent in vacuo from the filtrate
  4. dissolutionDissolve the resultant residue in 80 ml ethyl ether
  5. filtrationfilter through a column of 45-50 g silica gel eluting with additional ethyl ether

Sources & evidence

ORD record
ord-987d1d0b591a4ef79b899ecc110a136f
Source dataset
uspto-grants-1980_01
Patent number
US04183923

Reaction notes

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