Water → 3-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid

HRID 709452Notes

Reaction equation

HRID 709452 reaction equation
C[O:2][C:3](=[O:31])[CH:4]([S:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:20])([CH3:19])[O:13][SiH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:8][CH:7]=1.O.[OH-].[Na+]>C1COCC1>[C:15]([SiH2:14][O:13][C:12]([CH3:20])([CH3:19])[C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH:4]([S:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[C:3]([OH:31])=[O:2])=[CH:11][CH:10]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 1317316773-[4-(Tert-butyl-dimethyl-silanyloxy-methyl)-phenyl]-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid methyl ester

Product 1

HCID 1317316793-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid methyl ester (4.93 g, 10.66 mmol) was dissolved in THF (100 mL) and water (50 mL) and cooled down to 0° C. NaOH (6.39 g, 159.88 mmol) was added and the resulting suspension was stirred stirring for 1 h without removing the cooling bath and another 28 h at ambient temperature. 2N HCl was added until pH 2 was reached and the mixture was extracted with EtOAc (3×100 mL). The combined organic layers were dried (MgSO4) and evaporated under reduced pressure to afford the crude product which was directly proceeded to the next step (4.79 g, 95.3%). 1H NMR (400 MHz, CDCl3): δ 7.16 (d, 2H), 7.06 (d, 2H), 6.99 (m, 2H), 6.85 (t, 2H), 4.62 (s, 2H), 3.38 (t, 1H), 3.09 (dd, 1H), 2.71-2.82 (m, 5H), 0.844 (s, 9H), 0.00 (s, 6H). Mass Spectrum: M−H+ 447.10.

Workup

  1. stirringstirring for 1 h
  2. customwithout removing the cooling bath
  3. customanother 28 h
  4. customat ambient temperature
  5. addition2N HCl was added until pH 2
  6. extractionthe mixture was extracted with EtOAc (3×100 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5344026b5668400f98417d4a651a730c
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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