Sodium Hydroxide → (2R)-3-[[4-[(4-cyclohexylphenyl)-[[4-(trifluoromethylsulfanyl)phenyl]carbamoylamino]methyl]benzoyl]amino]-2-hydroxypropanoic acid

HRID 967648Notes

Reaction equation

HRID 967648 reaction equation
C[O:2][C:3](=[O:44])[C@H:4]([OH:43])[CH2:5][NH:6][C:7](=[O:42])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([S:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=2)=[O:29])[C:15]2[CH:20]=[CH:19][C:18]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:10][CH:9]=1.[OH-].[Na+]>C(O)C>[CH:21]1([C:18]2[CH:17]=[CH:16][C:15]([CH:14]([NH:27][C:28]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([S:37][C:38]([F:41])([F:39])[F:40])=[CH:33][CH:32]=3)=[O:29])[C:11]3[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][C@@H:4]([OH:43])[C:3]([OH:44])=[O:2])=[O:42])=[CH:9][CH:10]=3)=[CH:20][CH:19]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67483231(R)-3-{4-[1-(4-cyclohexylphenyl)-3-(4-trifluoromethylsulfanylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid methyl ester

Product 1

HCID 67485123(2R)-3-[[4-[(4-cyclohexylphenyl)-[[4-(trifluoromethylsulfanyl)phenyl]carbamoylamino]methyl]benzoyl]amino]-2-hydroxypropanoic acidYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-3-{4-[1-(4-Cyclohexylphenyl)-3-(4-trifluoromethylsulfanylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid methyl ester (0.32 g, 0.508 mmol) was dissolved in ethanol (15 mL) and sodium hydroxide (4 N, 0.76 mL, 3.05 mmol) was added. The reaction mixture was stirred for 1.5 hour. The reaction was evaporated and added water (15 mL) and acidified with hydrochloric acid (4 N, 0.8 mL). The mixture was extracted with ethyl acetate (20 mL). The aqueous phase was extracted once more with ethyl acetate (15 mL) and the combined organic phases were washed with water (3×10 mL), dried over magnesium sulphate, filtered and concentrated to give the title compound (0.3 g).

Workup

  1. customThe reaction was evaporated
  2. additionadded water (15 mL)
  3. extractionThe mixture was extracted with ethyl acetate (20 mL)
  4. extractionThe aqueous phase was extracted once more with ethyl acetate (15 mL)
  5. washthe combined organic phases were washed with water (3×10 mL)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-da921ab60e6f4ad8ad12a9babdc36aa0
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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