Lithium Hydroxide → HCID 178491758, compound

HRID 1517376Notes

Reaction equation

HRID 1517376 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][N:11]([CH3:25])[S:12]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([O:22][CH3:23])=[CH:17][C:16]=3[CH3:24])(=[O:14])=[O:13])[NH:7][C:6]=2[C:26]=1[C:27]([O:29]CC)=[O:28].[Li+].[OH-]>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][N:11]([CH3:25])[S:12]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([O:22][CH3:23])=[CH:17][C:16]=3[CH3:24])(=[O:14])=[O:13])[NH:7][C:6]=2[C:26]=1[C:27]([OH:29])=[O:28]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178469422HCID 178469422, compound

Product 1

HCID 178491758HCID 178491758, compoundYield 20%

Reagents, catalysts & solvents 1

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

Procedure

Ethyl 6-fluoro-2-((4-methoxy-N,2,6-trimethylphenylsulfonamido)methyl)-1H-benzo[d]imidazole-7-carboxylate (F-20) (2.4 mmol, 1 eq.) was hydrolysed with LiOH in THF/H2O (1:1). After the hydrolysis, the solvent was removed completely from the reaction mixture in vacuo and the residue was taken up in water and washed with ethyl acetate. The aqueous phase was adjusted to pH=4 and then extracted with ethyl acetate. The free acid 6-fluoro-2-((4-methoxy-N,2,6-trimethylphenyl-sulfonamido)methyl)-1H-benzo[d]imidazole-7-carboxylic acid (ACI-20) obtained in this way was coupled with 9-pyridin-4-Yl-3,9-diazaspiro[5.5]undecane dihydrochloride (AMN-01) under standard peptide coupling conditions. Yield: 20%

Workup

  1. customAfter the hydrolysis
  2. customthe solvent was removed completely from the reaction mixture in vacuo
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-028641df77b4405d97819137aa612b6b
Source dataset
uspto-grants-2012_07
Patent number
US08232288B2

Reaction notes

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