Isobutyraldehyde → HCID 58460176, compound

HRID 1946529Notes

Reaction equation

HRID 1946529 reaction equation
C([O-])(=O)C.[NH4+:5].[C:6]1([CH2:12][O:13][C:14](=[O:24])[CH2:15][C:16]2[CH2:21][CH2:20][CH2:19][C:18](=O)[C:17]=2O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:25](=O)[CH:26]([CH3:28])[CH3:27].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C@@H:37]([NH2:39])[CH3:38])=[CH:33][CH:32]=1>C(Cl)(Cl)Cl.C(O)(=O)C>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C@@H:37]([N:39]2[C:17]3[CH:16]([CH2:15][C:14]([O:13][CH2:12][C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=4)=[O:24])[CH2:21][CH2:20][CH2:19][C:18]=3[N:5]=[C:25]2[CH:26]([CH3:28])[CH3:27])[CH3:38])=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 6561IsobutyraldehydeHCID 517165Ammonium AcetateHCID 1550852(S)-(-)-1-(4-chlorophenyl)ethylamineHCID 58460172HCID 58460172, compound

Product 1

HCID 58460176HCID 58460176, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

Acetic acid (0.572 mL) and ammonium acetate (154 mg) were mixed, to this were added Intermediate 65 (521 mg), isobutyraldehyde (0.196 mL) and (1S)-1-(4-chlorophenyl)ethanamine (0.362 mL) in chloroform (1.5 mL) and heated to reflux overnight. The mixture was reduced in vacuo and purified by column chromatography (0-100% ethyl acetate in cyclohexane). The appropriate fractions were concentrated in vacuo to yield 171 mg of the title compound. LC/MS MH+ 452, Rt 3.50 mins (5 min system, High ph).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. custompurified by column chromatography (0-100% ethyl acetate in cyclohexane)
  4. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-fd586982ccf247f5a357b3a86c0e970f
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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