Ethyl Acetate → 9H-fluoren-9-ylmethyl-6-[1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1(4H)-carboxylate

HRID 277853Notes

Reaction equation

HRID 277853 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]3[NH:21][CH:20]([CH3:22])[O:19][C:18]([CH3:24])([CH3:23])[C:17]=3[CH:25]=2)=[CH:11][CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:27]([O:29][CH2:30][CH:31]1[C:43]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:28].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O1CCOCC1.O>[CH:42]1[C:43]2[CH:31]([CH2:30][O:29][C:27]([N:21]3[C:16]4[CH:15]=[CH:14][C:13]([C:12]5[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:9]=[CH:10][CH:11]=5)=[CH:25][C:17]=4[C:18]([CH3:24])([CH3:23])[O:19][CH:20]3[CH3:22])=[O:28])[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]=2[CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 54467598tert-Butyl-5-(2,4,4-trimethyl-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrole-1-carboxylate

Product 1

HCID 183745569H-fluoren-9-ylmethyl-6-[1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1(4H)-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl-5-(2,4,4-trimethyl-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrole-1-carboxylate (1.7 g, 4.96 mmol), 9-fluorenylmethyl chloroformate (1.92 g, 7.5 mL), sodium carbonate (4 g, 37 mmol) in dioxane (50 mL) and water (50 mL) was stirred at room temperature under a blanket of nitrogen for 6 hours. Ethyl acetate (100 mL) was added and organic layer was separated, dried (MgSO4), and evaporated. The residue was purified by a silica gel column chromatography (hexane:ethyl acetate/6:1) to afford 9H-fluoren-9-ylmethyl-6-[1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1(4H)-carboxylate as a clean oil.

Workup

  1. customorganic layer was separated
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by a silica gel column chromatography (hexane:ethyl acetate/6:1)

Sources & evidence

ORD record
ord-a1b8549a6c96435bacd2ba8eec3b0983
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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