Hydrochloric Acid → HCID 66970543, compound

HRID 1455533Notes

Reaction equation

HRID 1455533 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]3[CH:16]=[CH:15][C:14](=[O:18])[N:13]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:12]=3[S:11][C:10]=2[C:25]([N:27]2[CH2:31][CH2:30][C@@H:29]([O:32]C3CCCCO3)[CH2:28]2)=[O:26])=[CH:4][C:3]=1[CH3:39].Cl.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]3[CH:16]=[CH:15][C:14](=[O:18])[N:13]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:12]=3[S:11][C:10]=2[C:25]([N:27]2[CH2:31][CH2:30][C@@H:29]([OH:32])[CH2:28]2)=[O:26])=[CH:4][C:3]=1[CH3:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68808277HCID 68808277, compound

Product 1

HCID 66970543HCID 66970543, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of Example 26 (5.8 g) in EtOH (180 ml) was treated with 1.3M HCl (32 ml). The mixture was stirred at ambient temperature overnight. The pH was adjusted to 8 using 2M sodium hydroxide. The resulting mixture was concentrated to remove the EtOH, and the solid was filtered off, washed with water, then reslurried in 25 ml water for 1 h. The suspension was filtered, washed with water, and the product was dried in a vacuum oven at 45° C. overnight. The beige solid was recrystallised from 19 volumes of EtOH, to give the title compound as a crystalline solid (3.52 g). δH (CDCl3) 9.65 (s, 1H), 7.65-7.50 (3H, m), 7.35-7.50 (2H, m), 7.25 (1H, d, J 9 Hz), 6.85-7.00 (3H, m), 6.40 (1H, d, J 9 Hz), 4.50 (1H, br s), 3.55-3.80 (4H, m), 2.25 (3H, br s), 1.95-2.05 (2H, m), 1.80 (1H, d, J 4 Hz). LCMS (ES+) RT 2.90 min, 464 (M+H)+.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customto remove the EtOH
  3. filtrationthe solid was filtered off
  4. washwashed with water
  5. waitreslurried in 25 ml water for 1 h
  6. filtrationThe suspension was filtered
  7. washwashed with water
  8. customthe product was dried in a vacuum oven at 45° C. overnight
  9. customThe beige solid was recrystallised from 19 volumes of EtOH

Sources & evidence

ORD record
ord-531adab7d9c74856a24c6954b8714ff2
Source dataset
uspto-grants-2009_01
Patent number
US07482452B2

Reaction notes

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