Sodium Hydroxide → HCID 10282370, compound

HRID 412461Notes

Reaction equation

HRID 412461 reaction equation
C[O:2][C:3](=[O:45])[C@H:4]([OH:44])[CH2:5][NH:6][C:7](=[O:43])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:33][CH:32]=2)[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=2)=[O:17])=[CH:10][CH:9]=1.[OH-].[Na+]>C(O)C>[C:25]([C:22]1[CH:23]=[CH:24][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:44])[C:3]([OH:45])=[O:2])=[O:43])=[CH:13][CH:12]=2)[C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:33][CH:32]=2)=[CH:20][C:21]=1[C:27]([F:28])([F:30])[F:29])#[N:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67483253HCID 67483253, compound

Product 1

HCID 10282370HCID 10282370, compoundYield 901.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-3-{4-[3-(4-Cyano-3-trifluoromethylphenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoyl-amino}-2-hydroxypropionic acid methyl ester (0.07 g, 0.124 mmol) was suspended in ethanol (3 mL) and sodium hydroxide (4 N, 0.19 mL, 0.742 mmol) was added. The reaction mixture was stirred for 1.5 hour, and concentrated to remove the ethanol. The residue was diluted with water (10 mL) and acidified with hydrochloric acid (4 N, 0.21 mL). The mixture was extracted with ethyl acetate (2×10 mL) and the combined organic phases were washed with water (3×10 mL), dried with magnesium sulphate and concentrated in vacuo to afford the title compound (0.68 g).

Workup

  1. concentrationconcentrated
  2. customto remove the ethanol
  3. additionThe residue was diluted with water (10 mL)
  4. extractionThe mixture was extracted 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-9e1a39833007492db018bb7263efd589
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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