Acetic Acid → HCID 136104127, compound

HRID 1181066Notes

Reaction equation

HRID 1181066 reaction equation
[C:1]([O:5][C:6](=[O:47])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27](B4OC(C)(C)C(C)(C)O4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:39][NH:40][C:41]([O:43][CH:44]([CH3:46])[CH3:45])=[O:42])([CH3:4])([CH3:3])[CH3:2].C(O)(=[O:50])C.OO.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:47])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][C:27]([OH:50])=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:39][NH:40][C:41]([O:43][CH:44]([CH3:45])[CH3:46])=[O:42])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 69232552HCID 69232552, compound

Product 1

HCID 136104127HCID 136104127, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

According to the procedure in Organic Synthesis, vol. V, p. 918, a solution of 3-[2-(isopropoxycarbonylamino-methyl)-4-(2-{5-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazol-4-yl}-ethoxy)-phenyl]-propionic acid tert-butyl ester (1.4 g, 2.16 mmol, Example 368, Step A) in THF (8 mL) was treated with glacial acetic acid (194 mg, 3.24 mmol) at 0° C. A solution of 30% H2O2 in water (4.75 mL) was diluted with H2O (1 mL) and added to the reaction mixture. The mixture was warmed to room temperature and treated with 1M aqueous Na2S2O3 solution (50 mL). The THF was removed under vacuum and the aqueous phase was extracted with ethyl acetate. The organic layer was washed with 1M Na2S2O3 (2×50 mL), dried (MgSO4), filtered, and concentrated to an oil containing (1.21 g). Purification using silica gel chromatography (1:1 ηεξανεσ:ετηψλ acetate) yielded the title compound as a white solid (1.10 g, 95%). 1H NMR (300 MHz CDCl3) δ 1.15 (d, 6H), 1.19 (s, 9H), 2.26 (s, 3H), 2.39 (t, 2H), 2.75 (t, 2H), 2.85 (t, 2H), 4.10 (t, 2H), 4.28 (d, 2H), 4.85 (m, 1H), 5.01 (br d, 1H), 6.63 (dd, 1H), 6.74 (m, 3H), 6.96 (d, 1 h), 7.70 (d, 2H); MS [EI+] m/z 539 (M+H).

Workup

  1. customAccording to the procedure in Organic Synthesis
  2. additionadded to the reaction mixture
  3. customThe THF was removed under vacuum
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. washThe organic layer was washed with 1M Na2S2O3 (2×50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. additioncontaining (1.21 g)
  10. customPurification

Sources & evidence

ORD record
ord-3a2f42be702b476c85d35da2bbaed823
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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