4-Toluenesulfonyl chloride → HCID 86757932, compound

HRID 840768Notes

Reaction equation

HRID 840768 reaction equation
[CH3:1][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([CH2:31][OH:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:3].[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>N1C=CC=CC=1>[CH3:25][C@:22]12[C@:21]3([CH3:26])[CH2:20][CH2:19][C@H:18]4[C:17]([CH3:27])([CH3:28])[C@@H:16]([OH:29])[CH2:15][CH2:14][C@:13]4([CH3:30])[C@H:12]3[CH2:11][CH2:10][C@@H:9]1[C@@H:8]1[C@@:7]3([CH2:31][O:32][C@H:4]1[C:2]([CH3:1])([CH3:3])[CH2:5][CH2:6]3)[CH2:24][CH2:23]2.[S:39]([C:36]1[CH:37]=[CH:38][C:33]([CH3:43])=[CH:34][CH:35]=1)([O-:29])(=[O:41])=[O:40]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 72326Betulin

Product 1

HCID 86757932HCID 86757932, compoundYield 142.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Betulin (3 g) and p-toluenesulfonyl chloride (2.52 g) were placed in dry pyridine (70 ml) at 3-5° C. After 72 hours at 3-5° C. the solution was poured into 100 ml of cracked ice and the resulting precipitate was washed with water (2×50 ml), 1% HCl (50 ml) and water (2×50 ml) and dried in an oven. Chromatography on a silica column (Ether:Hexane=25:75) gave 2.96 g of allobetulin tosylate as white crystals mp. 180-182.6° C. (dec); IR (KBr) 2944, 2864, 1489, 1451, 1363, 1337, 1174, 1098, 1036, 925, 905, 875, 812, 685, 560 cm−1; 1H NMR (CDCl3) δ 7.8(D, 2H, benz-Tos), 7.37(D, 2H, benz-Tos), 4.22(DD, 1H, 3H), 3.76(D, 1H, 28H, J=11 Hz), 3.52(S, 1H, 19H), 3.39(D, 1H, 28H, J=11 Hz), 2.44(S, 3H, Tos-Me), 0.8, 0.8, 0.83, 0.92, 0.93, 0.96, 0.99, (all S, 7×3H, 23-, 24-, 25-, 26-, 27-, 29-, 30-Me), 0.6-1.86(complex CH—, CH2—, 25H); 13C NMR (CDCl3) δ 144.46, 135.08, 129.88, 129.88, 127.83, 127.83, 91.18, 88.10, 71.42, 55.93, 51.1, 46.98, 41.65, 40.9, 40.76, 38.95, 38.84, 37.16, 36.92, 36.46, 34.29, 33.97, 32.90, 29.03, 27.98, 26.59, 26.43, 25.04, 24.76, 21.86, 21.23, 18.47, 16.67, 16.43, 15.87, 13.69.

Workup

  1. washthe resulting precipitate was washed with water (2×50 ml), 1% HCl (50 ml) and water (2×50 ml)
  2. customdried in an oven

Sources & evidence

ORD record
ord-08c24183358742709890a6df89945408
Source dataset
uspto-grants-2002_04
Patent number
US06369101B1

Reaction notes

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