HCID 70896602, compound → HCID 49850147, compound

HRID 403133Notes

Reaction equation

HRID 403133 reaction equation
C([O:5][C:6]1[CH:38]=[CH:37][CH:36]=[CH:35][C:7]=1[CH2:8][N:9]([CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][CH2:24]1)[CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)(C)(C)C>CCOC(C)=O.Cl>[NH2:12][CH2:11][CH2:10][N:9]([CH2:8][C:7]1[CH:35]=[CH:36][CH:37]=[CH:38][C:6]=1[OH:5])[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 1

HCID 70896602HCID 70896602, compound

Product 1

HCID 49850147HCID 49850147, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 24 (0.8 g, 1.52 mmol) was dissolved in 25 mL EtOAc saturated with HCl and stirred for 3 hr. The solvent was evaporated to dryness. The residue was purified on a silica gel TLC plate that was developed in 8% methanolic NH3 (7 M NH3 in methanol/92% CH2Cl2. The product was obtained as white solid (61%). 1H NMR (CDCl3) δ 7.276 (m, 2H, Ar), 7.208 (m, 2H, Ar), 7.165 (m, 2H, Ar), 6.972 (dd, 1H, Ar), 6.822 (dd, 1H, Ar), 6.769 (ddd, 1H, Ar), 3.744 (s, 2H, —CH2), 3.013, (d, 2H, —CH2—), 2.902 (t, 2H, —CH2—), 2.596 (m, 4H, —CH2—CH2), 2.473 (m, 1H, —CH—), 2.356 (t, 2H, —CH2—), 2.023 (ddd, 2H, —CH2—), 1.784 (m, 6H). Mass Spec.=368.27 (M+H)+.

Workup

  1. customThe solvent was evaporated to dryness
  2. customThe residue was purified on a silica gel TLC plate that

Sources & evidence

ORD record
ord-77c3b00dafe2430997e516d21e0a981d
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

Loading…