Hydrochloric Acid → 4-(2-(5-((Tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acid

HRID 1685345Notes

Reaction equation

HRID 1685345 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[S:18][C:19]([S:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([C:29]([O:31]C)=[O:30])[C:24]=3[F:33])=[CH:20][N:21]=2)=[N:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[S:18][C:19]([S:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([C:29]([OH:31])=[O:30])[C:24]=3[F:33])=[CH:20][N:21]=2)=[N:14][CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59200482Methyl 4-(2-(5-((tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinate

Product 1

HCID 592004044-(2-(5-((Tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-(2-(5-((tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinate (1.28 g, 2.60 mmol) in tetrahydrofuran (40 mL) was treated with sodium hydroxide (5N, 3.12 mL, 15.6 mmol) at 23° C. The reaction was stirred for 2 hours, then acidified with conc. HCl to pH ˜2.0. Water was then added and the aqueous phase was extracted with ethyl acetate/THF. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (1.08 g, 87%) as a solid which was used as such in the next reaction.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate/THF
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f937941bd73b4ee3ae3f4db29985ab76
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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