Isobutyraldehyde → HCID 58460189, compound

HRID 1946533Notes

Reaction equation

HRID 1946533 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.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C@H:32]([NH2:34])[CH3:33])=[CH:28][CH:27]=1.[CH:35](=O)[CH:36]([CH3:38])[CH3:37]>C(O)(=O)C.C(Cl)(Cl)Cl>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C@H:32]([N:34]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:35]2[CH:36]([CH3:38])[CH3:37])[CH3:33])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 6561IsobutyraldehydeHCID 517165Ammonium AcetateHCID 1715226(1R)-1-(4-chlorophenyl)ethan-1-amineHCID 58460172HCID 58460172, compound

Product 1

HCID 58460189HCID 58460189, 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 (0.560 g), (1R)-1-(4-chlorophenyl)ethanamine (0.362 mL) and isobutyraldehyde (0.196 mL), the mixture dissolved in chloroform (2 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 the racemic mixture of the desired regioisomer. LC/MS MH+ 452, Rt 3.50 mins (5 min run, 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
  6. additionthe racemic mixture of the desired regioisomer
  7. customLC/MS MH+ 452, Rt 3.50 mins (5 min run, High pH)

Sources & evidence

ORD record
ord-912fc0280a794aaf9f764056907dab79
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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