Hydrochloric Acid → HCID 89650866, compound

HRID 2174231Notes

Reaction equation

HRID 2174231 reaction equation
[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([C:19]([O:21]CC)=[O:20])=[CH:8][N:7]=1)[CH3:2].Cl>[OH-].[Na+].C1COCC1>[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([C:19]([OH:21])=[O:20])=[CH:8][N:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89650816HCID 89650816, compound

Product 1

HCID 89650866HCID 89650866, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of iv (0.479 g, 1.46 mmol) in 2M NaOH (aq, 15 mL) and THF (2 mL) was stirred at 65° C. for 24 h. The mixture was cooled to 0° C. and the pH adjusted to pH˜2-3 using conc. HCl (35%). The resulting tan precipitate was filtered, washed with water, air-dried and further dried in vacuo to give compound v (0.321 g, 1.07 mmol, 73%) as a tan powder. 1H NMR (300 MHz, DMSO-d6): δ 10.47 (1H, br s), 9.90 (1H, br s), 8.84 (1H, app. t), 8.72 (1H, s), 7.65 (2H, d, J 7.7), 7.42 (2H, t, J 7.7), 7.21 (1H, t, J 7.2), 3.12-3.01 (2H, m), 0.90 (3H, t, J 7.2); [M+H]+ m/z=302.2.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationThe resulting tan precipitate was filtered
  3. washwashed with water
  4. customair-dried
  5. customfurther dried in vacuo

Sources & evidence

ORD record
ord-9180b164eef642f4a8fc6f8a75d58fa7
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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