Isobutyraldehyde → HCID 58460175, compound

HRID 1946531Notes

Reaction equation

HRID 1946531 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.[C:25]1([C@H:31]([NH2:33])[CH3:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH:34](=O)[CH:35]([CH3:37])[CH3:36]>C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:37][CH:35]([C:34]1[N:33]([C@@H:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:32])[C:17]2[CH:16]([CH2:15][C:14]([O:13][CH2:12][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:24])[CH2:21][CH2:20][CH2:19][C:18]=2[N:5]=1)[CH3:36]

Participants

7

Reactant 4

HCID 6561IsobutyraldehydeHCID 517165Ammonium AcetateHCID 6431891-Phenethylamine, (+)-HCID 58460172HCID 58460172, compound

Product 1

HCID 58460175HCID 58460175, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

Ammonium acetate (0.154 g) was dissolved in acetic acid (0.572 mL), to this was added Intermediate 65 (0.615 g), (1R)-1-phenylethanamine (0.362 mL) and isobutyraldehyde (0.216 mL, 2.363 mmol). The mixture was dissolved 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 224 mg. LC/MS, MH+ 417, Rt 3.33 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
  5. customto yield 224 mg
  6. customLC/MS, MH+ 417, Rt 3.33 mins (5 min system, High ph)

Sources & evidence

ORD record
ord-f117687bd83e4f3a9e27822d41ecdfea
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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