Lithium hydroxide, monohydrate → HCID 57635204, compound

HRID 2110227Notes

Reaction equation

HRID 2110227 reaction equation
[CH3:1][C:2]([CH3:29])([CH3:28])[C@H:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]2[CH2:20][CH2:19][CH2:18][N:17]([CH3:21])[CH2:16][C:15]=12)=[O:10])[C:4]([O:6]C)=[O:5].O.[OH-].[Li+]>C1COCC1.O>[CH3:1][C:2]([CH3:29])([CH3:28])[C@H:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:14]2[CH2:20][CH2:19][CH2:18][N:17]([CH3:21])[CH2:16][C:15]=12)=[O:10])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57635261HCID 57635261, compound

Product 1

HCID 57635204HCID 57635204, compoundYield 87%

Reagents, catalysts & solvents 1

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

Procedure

A solution of Compound 467 (0.63 g, 1.58 mmol) and lithium hydroxide monohydrate (0.33 g, 7.90 mmol) in THF/water (10 mL, 4:1) was stirred from 0° C. to room temperature overnight. After evaporation of THF, the residue was acidified with 1N HCl to pH2 and extracted twice with 20% iPrOH/DCM. The combined organic extracts were evaporated to give Compound 471 (87% yield). LCMS (+ESI) m/z 385.0 [M+H]+.

Workup

  1. customAfter evaporation of THF
  2. extractionextracted twice with 20% iPrOH/DCM
  3. customThe combined organic extracts were evaporated

Sources & evidence

ORD record
ord-7f8b1d6e7e2e4802bd93b9ffcff569b8
Source dataset
uspto-grants-2009_04
Patent number
US07517874B2

Reaction notes

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