Sodium Hydroxide → HCID 59761470, compound

HRID 544943Notes

Reaction equation

HRID 544943 reaction equation
[C:1]([O:5][C:6]([N:8]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[S:11][C:10]=1[C:21]([O:23]C)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[S:11][C:10]=1[C:21]([OH:23])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67148808HCID 67148808, compound

Product 1

HCID 59761470HCID 59761470, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 3-(bis(tert-butoxycarbonyl)amino)-5-(4-chlorophenyl)thiophene-2-carboxylate a (0.135 g, 0.29 mmol) in 1:1 THF/MeOH (2 mL) at rt was added a 3 N aq NaOH (1 mL) and the resulting mixture was warmed to 65° C. for 30 min then cooled to rt and concentrated to remove the volatile solvents. The remaining aqueous portion was cooled in an ice bath and 1 N aq HCl was added until pH ˜2 was reached. The slurry was stirred for 1 h then collected the resulting solid by vacuum filtration, rinsed with water and dried under vacuum to afford 86 mg (66%) of an off-white solid as compound b. HPLC Ret time=4.32 min.

Workup

  1. temperaturethen cooled to rt
  2. concentrationconcentrated
  3. customto remove the volatile solvents
  4. temperatureThe remaining aqueous portion was cooled in an ice bath
  5. addition1 N aq HCl was added until pH ˜2
  6. customthen collected the resulting solid
  7. filtrationby vacuum filtration
  8. washrinsed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-b1d4592918f74fa39f7a8035c969865c
Source dataset
uspto-grants-2011_05
Patent number
US07935696B2

Reaction notes

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