Methanol → HCID 70976204, compound

HRID 535538Notes

Reaction equation

HRID 535538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH:23]([CH3:29])[C:24]([O:26]CC)=[O:25])=[N:13]2)=[O:10])=[CH:4][CH:3]=1.CO.[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:11][N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH:23]([CH3:29])[C:24]([OH:26])=[O:25])=[N:13]2)=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 70975846HCID 70975846, compound

Product 1

HCID 70976204HCID 70976204, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 109C (1.4 g, 3.4 mmol) in THF (8 mL), water (4 mL), and MeOH (8 mL) was added 5M NaOH (3.4 mL, 17 mmol). After stirring at room temperature for 16 hours, the reaction mixture was concentrated to half the volume, diluted to 10 mL (water), washed with DCM, acidified to pH˜2 with aq 3N HCl, and filtered to obtain the precipitated product: 1H NMR (300 MHz, DMSO-d6) δ 12.72 (s, 1H), 11.60 (s, 1H), 8.33 (d, J=7.7, 1H), 8.03-7.97 (m, 2H), 7.91 (ddd, J=8.2, 6.7, 4.0, 1H), 7.41 (s, 4H), 4.40 (q, J=7.1, 1H), 3.69 (s, 2H), 1.45 (d, J=7.1, 3H); MS (ESI+) M/Z 386 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated to half the volume
  2. additiondiluted to 10 mL (water)
  3. washwashed with DCM
  4. filtrationfiltered
  5. customto obtain the precipitated product

Sources & evidence

ORD record
ord-1c7ce8262f654a348e25bf431b906b05
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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