HCID 71077066, compound → HCID 86714065, compound

HRID 576361Notes

Reaction equation

HRID 576361 reaction equation
C([O:9][CH2:10][C:11]1[CH:16]=[C:15]([C@H:17]2[C@H:22]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:21]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:20]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@@H:19]([CH2:47][O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[O:18]2)[CH:14]=[CH:13][C:12]=1[Cl:56])(=O)C1C=CC=CC=1>C1COCC1.CO.O>[Cl:56][C:12]1[CH:13]=[CH:14][C:15]([C@H:17]2[C@H:22]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C@@H:21]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:20]([O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C@@H:19]([CH2:47][O:48][CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[O:18]2)=[CH:16][C:11]=1[CH2:10][OH:9]

Participants

3

Reactant 1

HCID 71077066HCID 71077066, compound

Product 1

HCID 86714065HCID 86714065, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of benzoate 104 (6.13 g, 7.97 mmol) in THF/MeOH/H2O (150 mL/5 mL/5 mL) was added LiOH monohydrate (1.0 g, 23.9 mmol) at room temperature. The mixture was stirred at room temperature for 15 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 105 (5.33 g, 10%), 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-1aa1f2f5237242fbb0c3f19d33d6b8b3
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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