Water → HCID 69103059, compound

HRID 2220390Notes

Reaction equation

HRID 2220390 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][N:20]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:21][C@@H:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[C:43](OC(=O)C)(=[O:45])[CH3:44].O>N1C=CC=CC=1>[C:43]([NH:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][N:20]([CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:21][C@@H:22]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 69103330HCID 69103330, compound

Product 1

HCID 69103059HCID 69103059, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 3-amino-4′-[2-[benzyl[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino]ethyl]-4-biphenylcarboxylate (532 mg) in pyridine (600 μl) was added acetic anhydride (400 μl) and stirred overnight at room temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride aqueous solution and brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 3-(acetylamino)-4′-[2-[benzyl[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino]ethyl]-4-biphenylcarboxylate (381 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated ammonium chloride aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-b550bf22c608467a9ab80c540ad4917e
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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