Hydrochloric Acid → HCID 131733866, compound

HRID 708854Notes

Reaction equation

HRID 708854 reaction equation
C(O[C:6]([N:8]([CH2:10][C:11]1[CH:16]=[C:15]([NH:17]C(OC(C)(C)C)=O)[CH:14]=[CH:13][C:12]=1[C:25]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26]1)C)=O)(C)(C)C.[ClH:33]>CCOC(C)=O.ClCCl>[ClH:33].[NH2:17][C:15]1[CH:14]=[CH:13][C:12]([C:25]2([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26]2)=[C:11]([CH2:10][NH:8][CH3:6])[CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118093092HCID 118093092, compound

Product 1

HCID 131733866HCID 131733866, compoundYield 111.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

15F (0.173 g, 0.386 mmol) was dissolved in EtOAc (3 mL) and dichloromethane (2 mL), then HCl (4M in dioxane) (2 mL, 8.00 mmol) was added. The reaction mixture was stirred for 6 h at rt. The solvent was removed under reduced pressure, and the residue was dried under high vacuum to give 15G (0.123 g, 99% yield) as an off-white solid. MS (ESI) m/z: 249.1[M+1]+. 1H NMR: (400 MHz, CD3OD) δ ppm 7.69 (1H, d, J=2.27 Hz), 7.59 (1H, d, J=8.34 Hz), 7.42 (1H, dd, J=8.34, 2.27 Hz), 4.38 (2H, s), 4.14 (2H, q, J=7.07 Hz), 2.84 (3H, s), 1.83 (2H, d, J=3.03 Hz), 1.31-1.39 (2H, m), 1.20 (3H, t, J=7.20 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-39b3e40098504995867289f0192392f0
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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