Iodobenzene diacetate → HCID 51356009, compound

HRID 2367551Notes

Reaction equation

HRID 2367551 reaction equation
[CH2:1]([C@H:3]1[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][C@@H:6]([CH2:16][OH:17])[O:5][CH2:4]1)[CH3:2].CC1(C)N([O])C(C)(C)CCC1.C(OI(C1C=CC=CC=1)OC(=O)C)(=[O:31])C>C(Cl)Cl>[CH3:14][C:12]([O:11][C:9]([N:8]1[C@H:3]([CH2:1][CH3:2])[CH2:4][O:5][C@H:6]([C:16]([OH:31])=[O:17])[CH2:7]1)=[O:10])([CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 76724Iodobenzene diacetateHCID 2724126TempoHCID 513540381,1-Dimethylethyl (2S,5R)-5-ethyl-2-(hydroxymethyl)-4-morpholinecarboxylate

Product 1

HCID 51356009HCID 51356009, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred solution of 1,1-dimethylethyl(2S,5R)-5-ethyl-2-(hydroxymethyl)-4-morpholinecarboxylate (2.52 g, 10.27 mmol) in CH2Cl2 (50 mL) that was cooled to 0° C. were added TEMPO (0.321 g, 2.054 mmol) and (diacetoxyiodo)benzene (7.28 g, 22.60 mmol). The ice bath was removed, and the reaction was allowed to warm to room temperature and stirred overnight. The reaction was quenched with CH3OH and then concentrated to afford the title compound (0.711 g) as a yellow oil. LC-MS (ES) m/z=260 [M+H]+.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched with CH3OH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c18a34fdf2ce4983a38fbd76b9981f33
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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