Sodium Carbonate → HCID 86586407, compound

HRID 1064758Notes

Reaction equation

HRID 1064758 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([C:24](=O)[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1.Cl.[NH2:28][OH:29].C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([C:24](=[N:28][OH:29])[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 9884652HCID 9884652, compound

Product 1

HCID 86586407HCID 86586407, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 136C (240 mg, 0.5 mmol) and hydroxylamine hydrochloride (139 mg, 2.00 mmol) were dissolved into methanol (2 mL) and treated with Na2CO3 (318 mg, 3.0 mmol). The suspension was stirred at room temperature overnight and then heated at 70° C. three days. The mixture was cooled to room temperature and filtered, the solids being rinsed with 50% MeOH/CH2Cl2. The filtrate was concentrated, then partitioned between water and MeOH/CH2Cl2; some clean product remained undissolved and was separated. The organic phase was concentrated, dissolved in a little methanol, and seeded with the previously collected product. After this material had crystallized, both crops of product were rinsed with methanol and permitted to dry to provide the title compound as a white microcrystalline solid (49% yield). 1HNMR (300 MHz, CDCl3) δ 1.18 (d, 3 H), 1.4-2.1 (m, 4 H), 2.2-2.6 (m, 3 H), 2.34 (s, 3 H), 3.00-3.12 (m, 2 H), 3.20-3.34 (m, 2 H), 6.49 (s, 1H), 7.41-7.48 (m, 3 H), 7.56-7.63 (m, 2 H), 7.68 (dd, 1 H), 7.70 (bs, 1 H), 7.88 (dd, 1 H).

Workup

  1. temperatureheated at 70° C. three days
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. washthe solids being rinsed with 50% MeOH/CH2Cl2
  5. concentrationThe filtrate was concentrated
  6. custompartitioned between water and MeOH/CH2Cl2
  7. customwas separated
  8. concentrationThe organic phase was concentrated
  9. dissolutiondissolved in a little methanol
  10. customAfter this material had crystallized
  11. washboth crops of product were rinsed with methanol
  12. customto dry

Sources & evidence

ORD record
ord-c69ddaa1c50a48c3b998df6b16ef72fe
Source dataset
uspto-grants-2005_11
Patent number
US06969730B2

Reaction notes

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