Sodium Hydroxide → HCID 59038348, compound

HRID 1058437Notes

Reaction equation

HRID 1058437 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:34])/[C:6](/[NH:13][C:14](=[O:33])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])=[CH:17][C:16]=1[Br:32])=[CH:7]/[C:8]1[S:9][CH:10]=[CH:11][N:12]=1>O1CCCC1.CO>[Br:32][C:16]1[CH:17]=[C:18]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])[CH:19]=[CH:20][C:15]=1[C:14]([NH:13]/[C:6](=[CH:7]\[C:8]1[S:9][CH:10]=[CH:11][N:12]=1)/[C:5]([OH:34])=[O:4])=[O:33]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 23560730HCID 23560730, compound

Product 1

HCID 59038348HCID 59038348, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 1N sodium hydroxide (0.16 mL, 0.16 mmol) was added to a solution of (Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(thiazol-2-yl)propenoic acid methyl ester (Example 153; 39.3 mg, 0.076 mmol) in tetrahydrofuran/methanol (2:1; 0.25 mL). After the solution had been allowed to stir at room temperature for 16 h, a second portion of 1N sodium hydroxide solution (0.05 mL) was added and the reaction was allowed to proceed for another 24 h at ambient temperature. The solvent was evaporated using a rotary evaporator then high vacuum. The de-esterification had not gone to completion, so the residue was re-dissolved in tetrahydrofuran/methanol (2:1; 0.25 mL) and treated with a solution of 1N sodium hydroxide (0.16 mL, 0.16 mmol). The reaction mixture was stirred for 16 h and after the solvents were removed in vacuo, the residue was purified by HPLC to give (Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(thiazol-2-yl)propenoic acid (14.8 mg, 39%).

Workup

  1. waitto proceed for another 24 h at ambient temperature
  2. customThe solvent was evaporated
  3. customa rotary evaporator
  4. dissolutionwas re-dissolved in tetrahydrofuran/methanol (2:1; 0.25 mL)
  5. stirringThe reaction mixture was stirred for 16 h
  6. customafter the solvents were removed in vacuo
  7. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-1743f8c2cbdc4798ac8466b2573eb631
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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