Isopropyl iodide → HCID 86604638, compound

HRID 2267633Notes

Reaction equation

HRID 2267633 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C@H:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:3]1[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].I[CH:28]([CH3:30])[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH:28]([N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C@H:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:3]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[C:2]1=[O:1])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 59863952HCID 59863952, compound

Product 1

HCID 86604638HCID 86604638, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl [(2R,3S)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]carbamate (67a) (125 mg, 0.352 mmol) in dry DMF (3 mL) under nitrogen was added 2-iodopropane (90 mg, 0.529 mmol) and powdered cesium carbonate (172 mg, 0.529 mmol). The mixture was stirred overnight at ambient temperature then diluted with water and extracted with ethyl acetate three times. The residue from the organic extract was purified by flash chromatography on silica gel eluting with 5:1 (v/v) hexane:ethyl acetate to afford the title compound (82 mg, 58%) as a white solid. TLC Rf=0.35 (5:1 hexane:ethyl acetate). 1H NMR (300 MHz, CDCl3) δ1.28 (d, 6H, J=7.0 Hz), 1.37 (s, 9H), 4.81 (m, 2H), 4.99 (m, 1H), 5.58 (d, 1H, J=7.0 Hz), 7.19-7.48 (m, 9H). MS APCI, m/z=397 (M+1). LC/MS: 2.75 min.

Workup

  1. extractionextracted with ethyl acetate three times
  2. extractionThe residue from the organic extract
  3. customwas purified by flash chromatography on silica gel eluting with 5:1 (v/v) hexane

Sources & evidence

ORD record
ord-c62ab63e16294a73b46bd67df13a8232
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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