HCID 66693523, compound → HCID 66693979, compound

HRID 1469194Notes

Reaction equation

HRID 1469194 reaction equation
C([O:9][CH2:10][C:11]1[CH:15]=[C:14]([C@H:16]2[C@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:20]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@H:19]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:18]([CH2:46][O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[O:17]2)[S:13][C:12]=1[Cl:55])(=O)C1C=CC=CC=1>C1COCC1.CO.O>[Cl:55][C:12]1[S:13][C:14]([C@H:16]2[C@H:21]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@@H:20]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@H:19]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C@@H:18]([CH2:46][O:47][CH2:48][C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[O:17]2)=[CH:15][C:11]=1[CH2:10][OH:9]

Participants

3

Reactant 1

HCID 66693523HCID 66693523, compound

Product 1

HCID 66693979HCID 66693979, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of benzoate 36 (4.5 g, 5.80 mmol) in THF/MeOH/H2O (30 mL/10 mL/10 mL) was added LiOH monohydrate (0.73 g, 17.4 mmol) at room temperature. The mixture was stirred at room temperature for 5 hours. The mixture was extracted with EtOAc/aq. saturated NH4Cl solution (100 mL/100 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to yield the title compound 37 (3.86 g, 99%), which was carried on to the next step without further purification.

Workup

  1. extractionThe mixture was extracted with EtOAc/aq
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2d190c04cd349209df9e4adb7fe935b
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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