Lithium Hydroxide → HCID 23508295, compound

HRID 1884277Notes

Reaction equation

HRID 1884277 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]([CH2:23][CH:24]([OH:36])[CH2:25][S:26][C:27]3[S:28][C:29]4C=CC=C[C:30]=4[N:31]=3)[C:20]([OH:22])=[O:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Li+]>O.C1COCC1>[F:37][C:2]([F:1])([F:38])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]([CH2:23][CH:24]([OH:36])[CH2:25][S:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[C:20]([OH:22])=[O:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 23508282HCID 23508282, compound

Product 1

HCID 23508295HCID 23508295, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-[(4′-Trifluoromethyl[1,1′-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-[2-benzothiazolylthio]-pentanoic acid: To a solution of 3-[(4′-trifluoromethyl[1,1′-biphenyl]-4-yl)sulfonyl]amino-[2-oxo-5-(thiazol-2-yl)thio]methyl]-tetrahydrofuran 14c (1.13 g, 2.2 mmol) in water (5 mL) and THF (5 mL) is slowly added lithium hydroxide (0.53 g, 22 mmol). The reaction is stirred for 2 hr, then concentrated to dryness. The reaction mixture is diluted with water and then the mixture is extracted with ethyl ether (2×25 mL) The ethyl ether layer is discarded and the aqueous layer is slowly acidified with 1N HCl to pH 5, and then extracted 3 times with ethyl acetate. The combined ethyl acetate layers are washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The solid is purified by prep HPLC to give the desired white solid product.

Workup

  1. concentrationconcentrated to dryness
  2. additionThe reaction mixture is diluted with water
  3. extractionthe mixture is extracted with ethyl ether (2×25 mL) The ethyl ether layer
  4. extractionextracted 3 times with ethyl acetate
  5. washThe combined ethyl acetate layers are washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe solid is purified by prep HPLC
  10. customto give the desired white solid product

Sources & evidence

ORD record
ord-ba6448494f8743dfb35bfec87b22f58d
Source dataset
uspto-grants-2004_07
Patent number
US06762198B2

Reaction notes

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