Lithium hydroxide, monohydrate → HCID 59487295, compound

HRID 2044173Notes

Reaction equation

HRID 2044173 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH:14][C:15]([C:17]2[C:18]([S:23][CH2:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:8]=1.CO.C1COCC1>O>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][CH2:25][CH2:24][S:23][C:18]2[C:17]([C:15]([NH:14][CH2:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([OH:34])=[O:5])=[O:16])=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 67521572HCID 67521572, compound2×

Product 1

HCID 59487295HCID 59487295, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 120 mg (2.92 mmol) of lithium hydroxide monohydrate in water (4 ml) was added to a solution of 320 mg (0.73 mmol) of 3-[[[2-[3-(4-fluorophenyl)-propylsulfanyl]-pyridine-3-carbonyl]amino]-methyl]-benzoic acid methyl ester (exemplary compound 129) in a MeOH/THF mixture (2:1 vv, 9 ml), and the mixture was stirred for 16 h at RT. Concentration in vacuo was then carried out. The residue was taken up in water and washed with EA. The aqueous phase was then adjusted to pH ˜2 with 2M hydrochloric acid at 0° C. The resulting precipitate was filtered off, taken up in toluene and concentrated in vacuo. The residue was washed with an ether/pentane mixture (1:4 vv), yielding 170 mg (0.4 mmol, 55%) of 3-[[[2-[3-(4-fluorophenyl)-propylsulfanyl]-pyridine-3-carbonyl]amino]-methyl]-benzoic acid. MS: m/z 425.1 [M+H]+.

Workup

  1. concentrationConcentration in vacuo
  2. washwashed with EA
  3. customwas then adjusted to pH ˜2 with 2M hydrochloric acid at 0° C
  4. filtrationThe resulting precipitate was filtered off
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with an ether/pentane mixture (1:4 vv)

Sources & evidence

ORD record
ord-16627d73869e43538efa0dff9a680f00
Source dataset
uspto-grants-2013_11
Patent number
US08586755B2

Reaction notes

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