Hydrochloric Acid → HCID 59753055, compound

HRID 1909778Notes

Reaction equation

HRID 1909778 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][O:7][C:8]1[CH:20]=[CH:19][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=1.[OH-].[Na+].[C:23]([O:27]C)(=[O:26])[CH:24]=[CH2:25].Cl>O1CCOCC1.ClCCl>[N:16]1[CH:17]=[CH:18][C:13]([O:12][C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:6][C@H:2]3[CH2:3][CH2:4][CH2:5][N:1]3[CH2:25][CH2:24][C:23]([OH:27])=[O:26])=[CH:20][CH:19]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 14798Sodium HydroxideHCID 59753057HCID 59753057, compound

Product 1

HCID 59753055HCID 59753055, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from Example 144 (50 mg, 0.15 mmol) was treated with 20% NaOH (5 ml) and extracted with EtOAc, dried over Na2SO4 and dried down to give the free base. Dichloromethane (3 ml) and methyl acrylate (0.4 ml, 2.8 mmol) were added and the mixture was stirred at rt overnight. The reaction mixture was dried down to give an oil. Excess 4.0M HCl in dioxane was added and the mixture was stirred overnight at rt. The solvent was removed in vacuo to give the title compound. (15 mg, 23%); LC/MS; m/z 343 (M+H) 99%; 1H NMR (DMSO-d6, 400 MHz) δ 1.79-2.29 (4H, m), 2.89 (2H, m), 3.16 (1H, m), 3.56-3.71 (3H, m), 3.97 (1H, m) 4.34-4.51 (2H, m), 7.18 (2H, d, J=8.8 Hz), 7.33 (2H, d, J=9.6 Hz), 7.43 (2H, d, J=7.2 Hz), 8.80 (2H, d, J=7.2 Hz)

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. customdried down
  4. customto give the free base
  5. customThe reaction mixture was dried down
  6. customto give an oil
  7. stirringthe mixture was stirred overnight at rt
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-22efec61c35645a49e7a03d20a48e462
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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