Water → HCID 86656353, compound

HRID 1942476Notes

Reaction equation

HRID 1942476 reaction equation
[OH:1][CH2:2][C:3]1([CH3:40])[C:8](=[O:9])[N:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]2[CH:16]=[C:17]([C:21]([N:23]([CH:37]([CH3:39])[CH3:38])[C@@H:24]3[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]3)=[O:22])[C:18]([CH3:20])=[CH:19][C:5]=2[O:4]1.[CH:41]([N:44]([CH:47]([CH3:49])C)[CH2:45]C)([CH3:43])C.N1CCCC1.[OH2:55]>O1CCCC1>[CH:37]([N:23]([C:21]([C:17]1[C:18]([CH3:20])=[CH:19][C:5]2[O:4][C:3]([CH3:40])([CH2:2][O:1][C:45]([N:44]3[CH2:41][CH2:43][CH2:49][CH2:47]3)=[O:55])[C:8](=[O:9])[N:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]=2[CH:16]=1)=[O:22])[C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:25]1)([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 67329605HCID 67329605, compound

Product 1

HCID 86656353HCID 86656353, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (3R)-3-[{[2-(hydroxymethyl)-4-(4-methoxybutyl)-2,7-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (60 mg), N,N′-carbonyldiimidazole (20 mg) in tetrahydrofuran (1 ml) was added diisopropylethylamine (95 μl), and the mixture was stirred at room temperature for one hour. To the reaction mixture was added pyrrolidine (10 μl), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and extracted with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (59 mg).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-25bcc4354ea74a4485ec3c6d5527fad4
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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