Hydrochloric Acid → HCID 57910785, compound

HRID 1644876Notes

Reaction equation

HRID 1644876 reaction equation
Cl.C([O:6][C:7]([C:9]1[N:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:39])([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]4[N:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[CH:27][N:26]=3)[CH:22]([CH3:24])[CH3:23])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1)=[CH2:8])CCC.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>CCO.O>[CH3:39][C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:11]=[N:10][C:9]([C:7](=[O:6])[CH3:8])=[CH:14][CH:13]=2)=[CH:16][CH:17]=1)([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:27][N:26]=1)[CH:22]([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid3×HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 57910794HCID 57910794, compound

Product 1

HCID 57910785HCID 57910785, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Hydrochloric acid (100 mL of a 1.0 M solution in EtOH) was added to a stirred solution of 7b (15.8 g, 30.9 mmol) in EtOH (25.0 mL) at 0° C. After approximately 15 min, a second portion of hydrochloric acid (150 mL of a 2.0 M aqueous solution) was added, and after another 15 min, a third portion of hydrochloric acid (100 mL of a 6.0 M aqueous solution) was added. After an additional 10 min, the reaction was warmed to rt and aged for 30 min. The reaction was diluted with water, recooled to 0° C. and neutralized by the addition of solid sodium bicarbonate. The resulting mixture was saturated with solid sodium chloride and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound 7c m/z (ES) 454 (MH)+. 1HNMR (500 MHz, CDCl3): δ 8.80 (d, 2H, J=4.8 Hz), 8.42 (d, 1H, J=3.0 Hz), 8.16 (d, 1H, J=8.7 Hz), 8.08 (d, 2H, J=8.5 Hz), 7.98 (d, 1H, J=8.9 Hz), 7.56 (d, 2H, J=8.5 Hz), 7.27 (m, 1H), 7.24 (dd, 1H, J=3.0, 8.7 Hz), 7.18 (d, 1H, J=8.9 Hz), 5.34 (s, 2H), 3.10 (m, 1H, J=6.7 Hz), 2.94 (s, 3H), 1.73 (s, 3H), 0.88 (d, 3H, J=6.7 Hz), 0.83 (d, 3H, J=6.8 Hz).

Workup

  1. waitafter another 15 min
  2. waitAfter an additional 10 min
  3. customrecooled to 0° C.
  4. extractionextracted twice with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43274a9b8e864e38b5bf78ef200b4db3
Source dataset
uspto-grants-2012_02
Patent number
US08124628B2

Reaction notes

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