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Hydroxide → (R)-3-{4-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino]-2-hydroxypropionic Acid

HRID 967632
Notes
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Reaction equation

HRID 967632 reaction equation
C([O:3][C:4](=[O:48])[C@H:5]([OH:47])[CH2:6][NH:7][C:8](=[O:46])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([C:34]2[CH:39]=[CH:38][C:37]([CH:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)=[CH:36][CH:35]=2)[C:17]([NH:19][C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=2)=[O:18])=[CH:11][CH:10]=1)C.[OH-]>C(O)C>[F:27][C:26]([F:28])([F:29])[C:24]1[CH:25]=[C:20]([NH:19][C:17](=[O:18])[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:8]([NH:7][CH2:6][C@@H:5]([OH:47])[C:4]([OH:48])=[O:3])=[O:46])=[CH:14][CH:13]=2)[C:34]2[CH:39]=[CH:38][C:37]([CH:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)=[CH:36][CH:35]=2)[CH:21]=[C:22]([C:30]([F:32])([F:33])[F:31])[CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 961HydroxideHCID 86586059(R)-3-(4-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino]-2-hydroxypropionic acid ethyl ester

Product 1

HCID 10168450(R)-3-{4-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino]-2-hydroxypropionic AcidYield 84.8%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Conditions

Temperature
25 °C

Procedure

(R)-3-(4-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino]-2-hydroxypropionic acid ethyl ester (0.26 g, 0.38 mmol) was dissolved in ethanol (96%, 15 mL) and added solution hydroxide (4 N, 0.57 mL, 2.3 mmol). After stirring at 25° C. for 1 hour the mixture was evaporated in vacuo, and the residue was added water (30 mL) and acidified with hydrochloric acid (4 N, 0.62 mL). The aqueous phase was extracted twice with ethyl acetate (25 mL and 10 mL) and the combined organic phases were washed with saturated sodium chloride:water (1:1), dried (magnesium sulphate) and concentrated in vacuo to afford 0.21 g of the title compound.

Workup

  1. customwas evaporated in vacuo
  2. additionthe residue was added water (30 mL)
  3. extractionThe aqueous phase was extracted twice with ethyl acetate (25 mL and 10 mL)
  4. washthe combined organic phases were washed with saturated sodium chloride:water (1:1)
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-804d46cfbd1a47c3a120145be71a127f
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06953812B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes