Ammonium Chloride → HCID 69103330, compound

HRID 2220389Notes

Reaction equation

HRID 2220389 reaction equation
[CH2:1]([N:8]([CH2:30][C@@H:31]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([N+:27]([O-])=O)[CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:27][C:19]1[CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:30][C@@H:31]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)=[CH:12][CH:13]=2)[CH:22]=[CH:21][C:20]=1[C:23]([O:25][CH3:26])=[O:24]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 69103358HCID 69103358, compound

Product 1

HCID 69103330HCID 69103330, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 4′[2-[benzyl[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino]ethyl]-3-nitro-4-biphenylcarboxylate (1.44 g) in ethanol (30 ml) and water (10 ml) were added iron (406 mg) and ammonium chloride (65 mg) and stirred under reflux for 1.5 hours. The mixture was filtrated through Celite pad and evaporated. The residue was dissolved with ethyl acetate, chloroform and methanol, washed with saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate and evaporated to give methyl 3-amino-4′-[2-[benzyl[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino]ethyl]-4-biphenylcarboxylate (1.18 g).

Workup

  1. temperatureunder reflux for 1.5 hours
  2. filtrationThe mixture was filtrated through Celite pad
  3. customevaporated
  4. dissolutionThe residue was dissolved with ethyl acetate, chloroform and methanol
  5. washwashed with saturated sodium bicarbonate aqueous solution and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-52bdcffac9db4cb7b72cd2d385ca44c2
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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