Sodium Hydroxide → HCID 69655920, compound

HRID 1830829Notes

Reaction equation

HRID 1830829 reaction equation
C[O:2][C:3](=[O:46])[C@@H:4]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38](=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([CH2:29][CH3:30])=[CH:15][C:16]2[CH:28]=[CH:27][C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][C:18]=3[CH:17]=2)=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)C.C1COCC1>[C:38]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[NH:31][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([CH2:29][CH3:30])=[CH:15][C:16]2[CH:28]=[CH:27][C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][C:18]=3[CH:17]=2)=[CH:8][CH:7]=1)[C:3]([OH:46])=[O:2])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69655903HCID 69655903, compound

Product 1

HCID 69655920HCID 69655920, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

(S)-2-(2-Benzoyl-phenylamino)-3-{4-[2-ethyl-3-(9H-fluoren-2-yl)-allyloxy]-phenyl}-propionic acid methyl ester (example 5) (700 mg, 1.15 mmol) was dissolved in a mixture of ethanol (20 ml) and THF (20 ml). 1N NaOH (10 ml) was added and the mixture was stirred for 16 h at 5° C. The mixture was concentrated in vacuo. 1N HCl and ethyl acetate (10 ml) was added. 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 500 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. addition1N HCl 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-3b8a570ff92f476d8ddf3a31cf857dae
Source dataset
uspto-grants-2006_06
Patent number
US07067530B2

Reaction notes

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