Sodium → HCID 86588353, compound

HRID 2214802Notes

Reaction equation

HRID 2214802 reaction equation
C([O:4][C@H:5]1[C@@H:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:8]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:7][C@@H:6]1[O:36][C@H:37]1[C@@H:49]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@H:48]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C@@H:47]([CH2:66][O:67][CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[O:46][C@@H:38]1[S:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=O)C.[Na]>C1(C)C=CC=CC=1.CO>[CH2:12]([O:11][C@H:10]1[C@H:9]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:8]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:7][C@H:6]([O:36][C@H:37]2[C@@H:49]([O:50][CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[C@H:48]([O:58][CH2:59][C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[C@@H:47]([CH2:66][O:67][CH2:68][C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)[O:46][C@@H:38]2[S:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:5]1[OH:4])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 25193754HCID 25193754, compound

Product 1

HCID 86588353HCID 86588353, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

Compound 14 (6 g, 5.9 mmol) was dissolved in 40 ml of a toluene/methanol (1/1) mixture). We then added sodium (cat.). After 15 min, the solution was neutralized with Amberlite resin IR 120 (H+), filtered and concentrated. Silica gel chromatography (elution: cyclohexane/ethyl acetate=3/1) of the crude product yielded 16 (5.45 g, 95%) in the form of a colorless syrup.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. washSilica gel chromatography (elution: cyclohexane/ethyl acetate=3/1) of the crude product

Sources & evidence

ORD record
ord-67f9a280564f429fa828360555b4e30c
Source dataset
uspto-grants-2006_09
Patent number
US07109182B2

Reaction notes

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