Ammonium Acetate → HCID 57956047, compound

HRID 561867Notes

Reaction equation

HRID 561867 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][O:41][CH3:42])=[CH:35][C:3]=1[CH2:4][N:5]([CH:32]1[CH2:34][CH2:33]1)[C:6](=[O:31])[CH:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]2[C:27]([Cl:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[Cl:30])=[CH:14][CH:13]=1)[C:8](=O)[CH3:9].C([O-])(=O)C.[NH4+:47].C([BH3-])#N.[Na+]>CO>[NH2:47][CH:8]([CH3:9])[CH:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]2[C:23]([Cl:30])=[CH:24][C:25]([CH3:29])=[CH:26][C:27]=2[Cl:28])=[CH:14][CH:13]=1)[C:6]([N:5]([CH2:4][C:3]1[CH:35]=[C:36]([CH2:39][CH2:40][O:41][CH3:42])[CH:37]=[CH:38][C:2]=1[Cl:1])[CH:32]1[CH2:34][CH2:33]1)=[O:31]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86635931HCID 86635931, compound

Product 1

HCID 57956047HCID 57956047, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2-Chloro-5-(2-methoxyethyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxobutanamide from the previous step (1 eq.) and ammonium acetate (10 eq.) were combined in MeOH (0.06 M). After the addition of sodium cyanoborohydride (1.2 eq.), the resulting reaction mixture was heated at reflux for 2 h. The volatiles were then removed in vacuo and the resulting residue partitioned between EtOAc and 1 N aq. NaOH. The aqueous wash was separated and back extracted with EtOAc. The combined organic extracts were then washed further with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. The crude product thus obtained was purified further by way of flash chromatography (SiO2, 96:4 (v/v) CH2Cl2: 2.0 M NH3 in MeOH) to reveal the title compound as a white froth. MS (ESI+): 635.3.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 2 h
  4. customThe volatiles were then removed in vacuo
  5. customthe resulting residue partitioned between EtOAc and 1 N aq. NaOH
  6. washThe aqueous wash
  7. customwas separated
  8. extractionback extracted with EtOAc
  9. washThe combined organic extracts were then washed further with water and brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-00dc65695dcb49119b41136333dc3bc2
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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