Water → HCID 24805122, compound

HRID 1908692Notes

Reaction equation

HRID 1908692 reaction equation
[C:1]12([CH2:15][CH:14]([NH:16][C:17](=[O:32])[NH:18][C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH:21]=[N:22][N:23]4C(OC)=O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7]1)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.[OH-].[Na+].O>CO>[NH:23]1[C:24]2[C:20](=[C:19]([NH:18][C:17]([NH:16][CH:14]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:7][C:1]4([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[CH2:15]3)=[O:32])[CH:27]=[CH:26][CH:25]=2)[CH:21]=[N:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 24805121HCID 24805121, compound

Product 1

HCID 24805122HCID 24805122, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 1C (4.06 mmol) was suspended in methanol (20 mL) and was treated with 5N methanolic NaOH (3.3 mL, 16.5 mmol). The mixture was stirred at room temperature for 45 min, then it was poured into H2O (100 mL). The precipitate that formed was collected by filtration and was air-dried to afford the title compound as an off-white solid, 794 mg (43%). 1H NMR (300 MHz, DMSO-d6) δ ppm 13.01 (br, 1H), 8.67 (s, 1H), 8.06 (s, 1H), 7.69 (d, J=7.5 Hz, 1H), 7.31 (d, J=7.8 Hz, 1H), 7.23 (J=7.8 Hz, 1H), 7.16 (m, 1H), 7.08 (d, J=8.5 Hz, 1H), 6.90 (td; J=7.5, 1.0 Hz; 1H), 6.80 (dd; J=7.9, 1.0 Hz; 1H), 6.72 (d, J=8.1 Hz, 1H), 4.98 (m, 1H), 2.24 (m, 1H), 1.33-1.82 (m, 11H). MS (ESI+) m/z 377 (M+H).

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. customwas air-dried

Sources & evidence

ORD record
ord-05fe9205d8804f2685661c7fdd535e56
Source dataset
uspto-grants-2013_12
Patent number
US08598220B2

Reaction notes

Loading…