Sodium Hydroxide → Rac.-(z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid

HRID 1058444Notes

Reaction equation

HRID 1058444 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:36])/[C:6](/[NH:15][C:16](=[O:35])[C:17]1[CH:22]=[CH:21][C:20]([CH:23]([OH:33])[CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[CH:19][C:18]=1[Cl:34])=[CH:7]/[C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[CH3:14]>CO.O1CCCC1>[Cl:34][C:18]1[CH:19]=[C:20]([CH:23]([OH:33])[CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[CH:21]=[CH:22][C:17]=1[C:16]([NH:15]/[C:6](=[CH:7]\[C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[CH3:14])/[C:5]([OH:36])=[O:4])=[O:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59038419Rac.-(z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester

Product 1

HCID 59038361Rac.-(z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acidYield 58%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

An aqueous 1N solution of sodium hydroxide (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-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester (Example 229; 70 mg, 0.14 mmol) in methanol/tetrahydrofuran (1:1; 2 mL). After the solution was stirred at room temperature for 5 h and the solvents were removed under reduced pressure. Water (5 mL) was added and the mixture was filtered through Celite®. The filter pad was washed with water (2 mL) and the combined filtrates were acidified with 1N hydrochloric acid solution (0.5 mL). The mixture was stirred for 1 h, then the solids were filtered off, 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-(2,4-dimethylthiazol-5-yl)propenoic acid (39.3 mg, 58% yield) as a colorless solid.

Workup

  1. customthe solvents were removed under reduced pressure
  2. additionWater (5 mL) was added
  3. filtrationthe mixture was filtered through Celite®
  4. washThe filter pad was washed with water (2 mL)
  5. stirringThe mixture was stirred for 1 h
  6. filtrationthe solids were filtered off
  7. washwashed with water
  8. customdried
  9. customcrystallized from tetrahydrofuran/methanol/water

Sources & evidence

ORD record
ord-22e70ba3ea1e42cd9e175c2c3d9c2f3f
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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