Lithium hydroxide, monohydrate → HCID 57659423, compound

HRID 217197Notes

Reaction equation

HRID 217197 reaction equation
C[O:2][C:3]([C:5]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][C:18]2[N:22]=[C:21]([C:23]3[O:31][C:30]4[CH:29]=[CH:28][N:27]=[CH:26][C:25]=4[CH:24]=3)[O:20][N:19]=2)[CH2:13][CH2:12]1)=[O:10])([CH3:7])[CH3:6])=[O:4].O[Li].O>C1COCC1.O>[C:3]([C:5]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][C:18]2[N:22]=[C:21]([C:23]3[O:31][C:30]4[CH:29]=[CH:28][N:27]=[CH:26][C:25]=4[CH:24]=3)[O:20][N:19]=2)[CH2:15][CH2:16]1)=[O:10])([CH3:6])[CH3:7])([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57659549HCID 57659549, compound

Product 1

HCID 57659423HCID 57659423, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A stirred solution of 4-(5-furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-ylmethyl)piperidine-1-carboxylic acid 1-methoxycarbonyl-1-methylethyl ester (Example 72, 43 mg, 100 μmol) in THF-H2O (3:1, 2 mL) was treated with LiOH.H2O (9 mg, 220 μmol). After 16 h, the THF was evaporated in vacuo, then the remainder was diluted with H2O (2 mL), before being washed with EtOAc (2×5 mL). The aqueous phase was neutralised with 1 M HCl, then the mixture was extracted with EtOAc (3×10 mL). The combined EtOAc extracts were dried (MgSO4), filtered, and concentrated to furnish the title compound: RT=2.74 min; m/z (ES+)=415.1 [M+H]+.

Workup

  1. customthe THF was evaporated in vacuo
  2. additionthe remainder was diluted with H2O (2 mL)
  3. washbefore being washed with EtOAc (2×5 mL)
  4. extractionthe mixture was extracted with EtOAc (3×10 mL)
  5. dry with materialThe combined EtOAc extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0a2872d1b023472e837175a4563e44df
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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