Sodium Hydroxide → (R)-3-{4-[3-[3-(tert-Butyldimethylsilanyloxymethyl)-4-trifluoromethoxyphenyl]-1-(4-cyclohexyl-phenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid

HRID 412468Notes

Reaction equation

HRID 412468 reaction equation
C[O:2][C:3](=[O:53])[C@H:4]([OH:52])[CH2:5][NH:6][C:7](=[O:51])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:39]2[CH:44]=[CH:43][C:42]([CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)=[CH:41][CH:40]=2)[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[C:21]([CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH:20]=2)=[O:17])=[CH:10][CH:9]=1.[OH-].[Na+]>C(O)C>[Si:32]([O:31][CH2:30][C:21]1[CH:20]=[C:19]([NH:18][C:16](=[O:17])[N:15]([CH2:14][C:11]2[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][C@@H:4]([OH:52])[C:3]([OH:53])=[O:2])=[O:51])=[CH:13][CH:12]=2)[C:39]2[CH:44]=[CH:43][C:42]([CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)=[CH:41][CH:40]=2)[CH:24]=[CH:23][C:22]=1[O:25][C:26]([F:28])([F:27])[F:29])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67483192(R)-3-{4-[3-[3-(tert-butyldimethylsilanyloxymethyl)-4-trifluoromethoxyphenyl]-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid methyl ester

Product 1

HCID 67483177(R)-3-{4-[3-[3-(tert-Butyldimethylsilanyloxymethyl)-4-trifluoromethoxyphenyl]-1-(4-cyclohexyl-phenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acidYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-3-{4-[3-[3-(tert-butyldimethylsilanyloxymethyl)-4-trifluoromethoxyphenyl]-1-(4-cyclohexyl-phenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid methyl ester (24 mg, 0.032 mmol) was dissolved in ethanol (1 mL) and sodium hydroxide (0.05 mL, 019 mmol) was added. The reaction mixture was stirred for 2 hours and concentrated to remove the ethanol. The residue was diluted with water (10 mL), acidified with hydrochloric acid (4 N, 0.3 mL) and extracted with ethyl acetate (2×10 mL). The combined organic phases were washed with water (3×10 mL) and dried with magnesium sulphate and concentrated in vacuo to give 17 mg of (R)-3-{4-[3-[3-(tert-butyldimethylsilanyloxymethyl)-4-trifluoromethoxyphenyl]-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid.

Workup

  1. concentrationconcentrated
  2. customto remove the ethanol
  3. additionThe residue was diluted with water (10 mL)
  4. extractionextracted with ethyl acetate (2×10 mL)
  5. washThe combined organic phases were washed with water (3×10 mL)
  6. dry with materialdried with magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a734692a04b4d5aa353e7e1aa944eab
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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