Methanol → HCID 90411306, compound

HRID 629813Notes

Reaction equation

HRID 629813 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:7]2[C:12]([O:14]C)=[O:13].CO.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:7]2[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 89501069HCID 89501069, compound

Product 1

HCID 90411306HCID 90411306, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Intermediate 4B (5.0 g, 13.50 mmol) in THF (60 mL)/MeOH (60 mL) was added 1N NaOH (40.5 ml, 40.5 mmol). After 24 h, the reaction mixture was concentrated and the remaining aqueous layer cooled to 0° C. and the pH was adjusted to 5 using 1.0N HCl solution. The solution was extracted with EtOAc (3×75 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated to give 4.75 g (99%) of Intermediate 4 as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.55 (dd, J=17.2, 7.8 Hz, 2H), 7.20 (t, J=7.8 Hz, 1H), 5.49-5.32 (m, 1H), 3.86-3.73 (m, 1H), 3.59-3.48 (m, 1H), 2.92-2.74 (m, 2H), 1.42 (d, J=12.9 Hz, 9H) ppm. MS (ESI) m/z: 255.9 (M+H-tBoc)+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionThe solution was extracted with EtOAc (3×75 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4a39d6d23fb24058bcdc82d9f80566d7
Source dataset
uspto-grants-2016_04
Patent number
US09315519B2

Reaction notes

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