Ethanol → HCID 10187617, compound

HRID 1830824Notes

Reaction equation

HRID 1830824 reaction equation
C[O:2][C:3](=[O:43])[C:4]([NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(C(=O)C1C=CC=CC=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[CH:8][CH:7]=1.[OH-].[Na+].[CH2:46]([OH:48])[CH3:47]>C1COCC1>[C:46]([C:42]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH:36][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)=[CH:8][CH:7]=1)[C:3]([OH:43])=[O:2])(=[O:48])[C:47]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86588384HCID 86588384, compound

Product 1

HCID 10187617HCID 10187617, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-(S)-2-(2-Benzoyl-phenylamino-3-[4-(3-biphenyl-4-yl-allyloxy)-phenyl]-propionic acid methyl ester (example 1) (400 mg, 0.7 mmol) was dissolved in a mixture of ethanol (15 ml) and THF (15 ml). 1N NaOH (3 ml) was added and the mixture was stirred for 1 h at room temperature. The mixture was concentrated in vacuo. Water (5 ml) and ethyl acetate (10 ml) was added. The mixture was neutralised with 1N HCl. The aqueous phase was isolated and extracted with ethyl acetate (×2) The organic layers were combined, washed with water, dried (MgSO4) and evaporated to give 400 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionWater (5 ml) and ethyl acetate (10 ml) was added
  3. customThe aqueous phase was isolated
  4. extractionextracted with ethyl acetate (×2) The organic layers
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-12ad88c0996543cd9e52bfaacde08384
Source dataset
uspto-grants-2006_06
Patent number
US07067530B2

Reaction notes

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