Water → 4-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-2-fluoro-benzoic acid

HRID 337217Notes

Reaction equation

HRID 337217 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[F:27].O.[OH-].[Li+]>O1CCCC1>[C:23]([O:22][C:20]([NH:19][CH:16]1[CH2:15][CH2:14][N:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[C:5]([F:27])[CH:6]=2)(=[O:12])=[O:11])[CH2:18][CH2:17]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 710602664-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-2-fluoro-benzoic acid methyl ester

Product 1

HCID 710601234-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-2-fluoro-benzoic acidYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-2-fluoro-benzoic acid methyl ester (0.8 g, 2.0 mmol) was added to a 1:1 mixture of water and tetrahydrofuran (20 ml) containing lithium hydroxide (0.8 g, 20.4 mmol) and the mixture was stirred at room temperature for 2 hours. After this time the mixture was concentrated to half the original volume and the remaining solution was acidified to pH 1 with 1M HCl. The resulting precipitate was collected by filtration, washed with water (10 ml) and dried under vacuum to give the title compound (0.82 g, 99% yield) as a white solid. Tr=1.80 min m/z (ES+) (M+Na+) 425.

Workup

  1. concentrationAfter this time the mixture was concentrated to half the original volume
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water (10 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6d17b60739cd426aa9219163a3f68b85
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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