Sodium Hydroxide → HCID 10209915, compound

HRID 1830827Notes

Reaction equation

HRID 1830827 reaction equation
C[O:2][C:3](=[O:44])[C@@H:4]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13]/[CH:14]=[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:36]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:29][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: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:44])=[O:2])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10210340HCID 10210340, compound

Product 1

HCID 10209915HCID 10209915, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(E)-(S)-2-(2-Benzoyl-phenylamino)-3-{4-[3-(9H-fluoren-2-yl)-allyloxy]-phenyl}-propionic acid methyl ester (example 3) (600 mg, 1.0 mmol) was dissolved in a mixture of ethanol (20 ml) and THF (10 ml). 1N NaOH (5 ml) was added and the mixture was stirred for 16 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 500 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-0a6cdb69282744c9bb42f131081fc809
Source dataset
uspto-grants-2006_06
Patent number
US07067530B2

Reaction notes

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