Sodium Hydroxide → 3-[(1-tert-Butoxycarbonyl-cyclobutylmethyl)-sulfamoyl]-benzoic acid

HRID 2170109Notes

Reaction equation

HRID 2170109 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10](=[O:25])(=[O:24])[NH:11][CH2:12][C:13]2([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][CH2:14]2)[CH:5]=1.[OH-].[Na+]>C1COCC1>[C:20]([O:19][C:17]([C:13]1([CH2:12][NH:11][S:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:26])=[O:2])(=[O:25])=[O:24])[CH2:14][CH2:15][CH2:16]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 667975353-[(1-tert-Butoxycarbonyl-cyclobutylmethyl)-sulfamoyl]-benzoic acid methyl ester

Product 1

HCID 667975323-[(1-tert-Butoxycarbonyl-cyclobutylmethyl)-sulfamoyl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[(1-tert-butoxycarbonyl-cyclobutylmethyl)-sulfamoyl]-benzoic acid methyl ester (step 3) (1.87 g, 4.88 mmol) in THF (25 ml) was treated with 2M NaOH (aq) (24.38 ml, 48.8 mmol) and stirred at RT for 2 h. The reaction mixture was partitioned between diethyl ether and water. The aqueous portion was separated and acidified to pH 1 with 2N HCl, and extracted with EtOAc, and the combined organic portions were washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title product; 1H NMR (400 MHz, CDCl3) δ 8.64 (1H, s), 8.33 (1H, d), 8.12 (1H, d), 7.67 (1H, t), 5.40 (1H, t), 3.24 (2H, d), 2.38 (2H, m), 1.97 (4H, m), 1.48 (9H, s). LC-MS Rt 1.13 mins; 314.1 [M+H]+ (−tBu), Method 2minLC_v003.

Workup

  1. customThe reaction mixture was partitioned between diethyl ether and water
  2. customThe aqueous portion was separated
  3. extractionextracted with EtOAc
  4. washthe combined organic portions were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a5e2a3f970f47b1a25984df3df2afd5
Source dataset
uspto-grants-2015_06
Patent number
US09050339B2

Reaction notes

Loading…