Lithium hydroxide, monohydrate → HCID 86714096, compound

HRID 2206808Notes

Reaction equation

HRID 2206808 reaction equation
[Br:1][C:2]1[C:14]([CH:15]2[C@H:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@@H:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:18]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[O:16]2)=[CH:13][C:12]([CH2:54][C:55]2[CH:60]=[CH:59][C:58]([O:61][CH2:62][CH3:63])=[CH:57][CH:56]=2)=[C:11]([Cl:64])[C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].O[Li].O>C1COCC1.CO.O>[Br:1][C:2]1[C:14]([CH:15]2[C@H:20]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C@@H:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:18]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[O:16]2)=[CH:13][C:12]([CH2:54][C:55]2[CH:60]=[CH:59][C:58]([O:61][CH2:62][CH3:63])=[CH:57][CH:56]=2)=[C:11]([Cl:64])[C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86714097HCID 86714097, compound

Product 1

HCID 86714096HCID 86714096, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 2-(2-bromo-6-chloro-5-(4-ethoxybenzyl)-3-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H- pyran-2-yl)phenoxy)acetate (1.09 g, 1.14 mmole) in a mixture of THF/MeOH/H2O (12 mL/4 mL/4 mL) was added LiOH.H2O (144 mg, 3.42 mmole). The resulting solution was stirred at rt overnight. The reaction mixture was concentrated in vacuo and diluted with water. The resulting solution was acidified with 1N—HCl solution followed by extraction with ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to yield the title compound (1.03 g, 98%) as a brown gum.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dd75b78eb234315af4c74ddfe1f2fd7
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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