Hydrochloric Acid → HCID 68996055, compound

HRID 985390Notes

Reaction equation

HRID 985390 reaction equation
C(OC([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:32])[C:24]2[C:29]([Cl:30])=[CH:28][N:27]=[CH:26][C:25]=2[Cl:31])=[CH:18][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)(C)(C)C.Cl>CCOC(C)=O.O1CCOCC1>[ClH:30].[NH2:8][C@@H:9]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:32])[C:24]2[C:29]([Cl:30])=[CH:28][N:27]=[CH:26][C:25]=2[Cl:31])=[CH:20][CH:21]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69000370HCID 69000370, compound

Product 1

HCID 68996055HCID 68996055, compoundYield 194%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of the compound of Intermediate 2 (70 g, 0.146 mol) in EtOAc (500 ml) and 1,4-dioxan (50 ml) was treated with a solution of HCl in EtOAc (500 ml, 3M), and stirred at room temperature for 4 h. The reaction was concentrated in vacuo to give a yellow solid which was triturated with Et2O then recrystallised (EtOAc/hexane) to give the title compound (59.3 g, 92%). δH (DMSO d6), 11.10 (1H, s), 8.70 (2H, s), 7.55 (2H, d, J 8.4 Hz), 7.25 (2H, d, J 8.4 Hz), 4.10 (3H, m), 3.10 (2H, m), 1.10 (3H, m); m/z (ES+, 70V) 382 (MH+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto give a yellow solid which
  3. customwas triturated with Et2O
  4. customthen recrystallised (EtOAc/hexane)

Sources & evidence

ORD record
ord-eb6e8410a55340a19e0d18eee6b88f50
Source dataset
uspto-grants-2005_03
Patent number
US06872719B1

Reaction notes

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