Lithium hydroxide, monohydrate → HCID 46847559, compound

HRID 1035691Notes

Reaction equation

HRID 1035691 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C:7]2[O:11][C:10]([NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:26][CH2:25][CH:24]([CH2:27][C:28]([O:30]CC)=[O:29])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[O:14])=[N:9][N:8]=2)=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.CO.O>[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C:7]2[O:11][C:10]([NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:22][CH2:23][CH:24]([CH2:27][C:28]([OH:30])=[O:29])[CH2:25][CH2:26]4)=[CH:17][CH:16]=3)=[O:14])=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86762091HCID 86762091, compound

Product 1

HCID 46847559HCID 46847559, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
4 °C

Procedure

0.1 g of ethyl (4-{4-[5-(4-fluorobenzyl)[1,3,4]oxadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetate (0.21 mmol, 1 eq.) and 0.036 g of lithium hydroxide hydrate (0.86 mmol, 4 eq.) are dissolved in 4 mL of a 2/1/1 mixture of tetrahydrofuran/methanol/water cooled to 4° C. using an ice bath. The reaction medium is stirred for 4 hours at room temperature. The solvents are evaporated off and an aqueous solution of SO2 is added. The solid obtained is filtered off, washed with water and dried to give 0.05 g of (4-{4-[5-(4-fluorobenzyl)[1.3.4]oxadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetic acid.

Workup

  1. customThe solvents are evaporated off
  2. additionan aqueous solution of SO2 is added
  3. customThe solid obtained
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-f77bb95377db44e0afdd6df3c24353ab
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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