Sodium Hydroxide → HCID 118061745, compound

HRID 920850Notes

Reaction equation

HRID 920850 reaction equation
[I:1][C:2]1[C:20]([C:21]([O:23]CC)=[O:22])=[C:5]2[CH2:6][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:8]3[CH2:12][O:11][CH2:10][C@@H:9]3[N:4]2[N:3]=1.[OH-].[Na+]>C1COCC1.O>[C:16]([O:15][C:13]([N:7]1[C@@H:8]2[CH2:12][O:11][CH2:10][C@@H:9]2[N:4]2[N:3]=[C:2]([I:1])[C:20]([C:21]([OH:23])=[O:22])=[C:5]2[CH2:6]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118062802HCID 118062802, compound

Product 1

HCID 118061745HCID 118061745, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of Intermediate 352D (0.85 g, 1.835 mmol) in THF (5 mL) was added a solution of NaOH (0.220 g, 5.50 mmol) in water (4 mL) and the reaction mixture was heated to 70° C. for 16 h. The reaction mixture was concentrated and the pH of the residue was adjusted to 4-5 using an aqueous solution of citric acid. The formed precipitate was filtered, washed with n-hexanes and dried to afford Intermediate 352E (0.48 g, 51%) as an off-white solid. MS(ES): −m/z=434 [M−H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 12.80-12.67 (m, 1H), 5.30 (d, J=18.5 Hz, 2H), 4.87 (dd, J=3.4, 6.8 Hz, 1H), 4.46-4.32 (m, 1H), 4.12-4.04 (m, 1H), 3.98-3.90 (m, 1H), 3.89-3.82 (m, 1H), 3.80-3.69 (m, 1H), 1.43 (s, 9H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe formed precipitate was filtered
  3. washwashed with n-hexanes
  4. customdried

Sources & evidence

ORD record
ord-fd7582ff59094765abfacaf7fbfd83bd
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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