Water → HCID 24805122, compound

HRID 1437491Notes

Reaction equation

HRID 1437491 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, 1H). 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-330846819e76456ca8cc3c25caa8c171
Source dataset
uspto-grants-2009_11
Patent number
US07622493B2

Reaction notes

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