Sodium Hydroxide → 4-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2-cyclopropylamino-3-fluorobenzoic acid

HRID 10298Notes

Reaction equation

HRID 10298 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][CH:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=[C:7]([F:24])[C:6]=1[NH:25][CH:26]1[CH2:28][CH2:27]1)C.[OH-].[Na+]>O1CCCC1.CO>[C:20]([O:19][C:17]([NH:16][CH:13]1[CH2:14][CH2:15][N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:29])=[O:3])=[C:6]([NH:25][CH:26]3[CH2:27][CH2:28]3)[C:7]=2[F:24])[CH2:12]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 210411824-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2-cyclopropylamino-3-fluorobenzoic acid ethyl ester

Product 1

HCID 219791744-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2-cyclopropylamino-3-fluorobenzoic acidYield 112.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2-cyclopropylamino-3-fluorobenzoic acid ethyl ester (Example 3j, 1.34 g, 3.29 mmol) and aqueous sodium hydroxide (2N, 20 mL) in tetrahydrofuran (20 mL) and methanol (20 mL) is refluxed for 1 hour. The solution is partially concentrated in vacuo, then acidified to pH 6 and extracted with chloroform. The combined organic extracts are dried over Na2SO4, filtered, and concentrated to give the title compound (1.40 g). 1H NMR (CDCl3): δ 7.59 (dd, 1H), 6.06 (dd, 1H), 4.80–4.70 (bd, 1H), 4.38–4.22 (m, 1H), 3.79–3.50 (m, 3H), 3.47–3.35 (m, 1H), 2.98–2.87 (m, 1H), 2.30–2.14 (m, 1H), 1.97–1.84 (m, 1H), 1.46 (s, 9H), 0.69–0.54 (m, 4H).

Workup

  1. concentrationThe solution is partially concentrated in vacuo
  2. extractionextracted with chloroform
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-389f49bf74d24494a85a7b0e9addedb2
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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