Sodium Hydroxide → HCID 10144633, compound

HRID 412463Notes

Reaction equation

HRID 412463 reaction equation
C[O:2][C:3](=[O:43])[C@H:4]([OH:42])[CH2:5][NH:6][C:7](=[O:41])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:31][CH:30]=2)[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:20]=2)=[O:17])=[CH:10][CH:9]=1.[OH-].[Na+]>C(O)C>[C:25]([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:42])[C:3]([OH:43])=[O:2])=[O:41])=[CH:13][CH:12]=2)[C:29]2[CH:34]=[CH:33][C:32]([CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)=[CH:31][CH:30]=2)[CH:24]=[CH:23][CH:22]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67483344HCID 67483344, compound

Product 1

HCID 10144633HCID 10144633, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-3-{4-[3-(3-tert-Butylphenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid methyl ester (0.11 g, 0.188 mmol) was dissolved in ethanol (4 mL) and sodium hydroxide (4 N, 0.28 mL, 1.128 mmol) was added. The reaction was stirred for 1.5 hour and concentrated in vacuo 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 afford the title compound (0.10 g).

Workup

  1. concentrationconcentrated in vacuo
  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-f00e929581774cefb4079da9a8dbb3b7
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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