Sodium Hydroxide → Rac.-(z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid

HRID 1058443Notes

Reaction equation

HRID 1058443 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]([CH:26]([OH: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]([CH:26]([OH: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 59038366Rac.-(z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester

Product 1

HCID 59038465Rac.-(z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acidYield 66%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

An aqueous solution of sodium hydroxide (1N; 0.5 mL, 0.5 mmol) was added to a solution of rac.-(Z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester (Example 228; 82 mg, 0.16 mmol) in methanol/tetrahydrofuran (1:1; 2 mL). The solution was stirred at room temperature for 16 h and the solvent was evaporated. Water (3 mL) was added and the mixture was acidified with 1N hydrochloric acid solution (0.25 mL). The precipitated solids were recovered by filtration, washed with water, dried and crystallized from tetrahydrofuran/methanol/water to give rac.-(Z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid (53 mg, 66% yield) as a colorless solid.

Workup

  1. customthe solvent was evaporated
  2. additionWater (3 mL) was added
  3. filtrationThe precipitated solids were recovered by filtration
  4. washwashed with water
  5. customdried
  6. customcrystallized from tetrahydrofuran/methanol/water

Sources & evidence

ORD record
ord-27424588d9114980a3f79f70f9741096
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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