Sodium Hydroxide → HCID 22638593, compound

HRID 2416210Notes

Reaction equation

HRID 2416210 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:16]3[N:17]=[C:18]([CH2:21][S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[S:19][CH:20]=3)[C:11](=[O:15])[NH:12]2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>C1COCC1>[C:25]1([S:22]([CH2:21][C:18]2[S:19][CH:20]=[C:16]([C:10]3[C:11](=[O:15])[NH:12][C:13]4[C:8]([CH:9]=3)=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=4)[N:17]=2)(=[O:24])=[O:23])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 69451465HCID 69451465, compound

Product 1

HCID 22638593HCID 22638593, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-benzenesulfonylmethyl-thiazol-4-yl)-1H-quinolin-2-one-7-carboxylic acid methyl ester (step (g), 0.9 g, 2.1 mmol) and THF (200 mL) was added 1N NaOH (4 mL). The solution was stirred at RT. After 2 h, an additional 4 mL of 1N NaOH was added. After an additional 3 h, 4 mL of 1N NaOH was added. After 24 h, TLC shows complete conversion. The solution was concentrated in vacuo and diluted with 100 mL of H2O. The aqueous solution was acidified with 2N HCl (aq) and a precipitate formed. The precipitate was filtered and dried in vacuo at 60° C. to give an off-white solid. MS m/z: 427.0 (M+1).

Workup

  1. waitAfter an additional 3 h
  2. waitAfter 24 h
  3. concentrationThe solution was concentrated in vacuo
  4. additiondiluted with 100 mL of H2O
  5. customa precipitate formed
  6. filtrationThe precipitate was filtered
  7. customdried in vacuo at 60° C.
  8. customto give an off-white solid

Sources & evidence

ORD record
ord-435ce7e254954b6d96720260a4841815
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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