Sodium Hydroxide → (Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid

HRID 1058441Notes

Reaction equation

HRID 1058441 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:39])/[C:6](/[NH:18][C:19](=[O:38])[C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:36])[CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[CH:22][C:21]=1[Cl:37])=[CH:7]/[C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2>CO.O1CCCC1>[Cl:37][C:21]1[CH:22]=[C:23]([C:26](=[O:36])[CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)[CH:24]=[CH:25][C:20]=1[C:19]([NH:18]/[C:6](=[CH:7]\[C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)/[C:5]([OH:39])=[O:4])=[O:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59038340(Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester

Product 1

HCID 59038327(Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acidYield 70.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

An aqueous 1N solution of sodium hydroxide (0.9 mL, 0.9 mmol) was added to a solution of (Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester (Example 226; 140 mg, 0.272 mmol) in methanol/tetrahydrofuran (1:1; 3.6 mL). The solution was stirred at room temperature for 16 h and the solvent was evaporated. Water (7 mL) was added and the mixture was extracted with diethyl ether. The diethyl ether extract was discarded and the water layer was filtered through Celite® and then acidified with 1N hydrochloric acid solution (1 mL). The resulting solid was filtered off, washed with water, dried and crystallized from tetrahydrofuran/methanol/water to give (Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid (96 mg, 70% yield) as a colorless solid.

Workup

  1. customthe solvent was evaporated
  2. additionWater (7 mL) was added
  3. extractionthe mixture was extracted with diethyl ether
  4. extractionThe diethyl ether extract
  5. filtrationthe water layer was filtered through Celite®
  6. filtrationThe resulting solid was filtered off
  7. washwashed with water
  8. customdried
  9. customcrystallized from tetrahydrofuran/methanol/water

Sources & evidence

ORD record
ord-193d863cb461447daae188b9438131d9
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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