Propargyl bromide → HCID 86604637, compound

HRID 2267629Notes

Reaction equation

HRID 2267629 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].[CH2:27](Br)[C:28]#[CH:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[O:1]=[C:2]1[N:8]([CH2:29][C:28]#[CH:27])[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]([CH3:23])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 59863952HCID 59863952, compound

Product 1

HCID 86604637HCID 86604637, compoundYield 80.8%

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) (160 mg, 0.451 mmol) in DMF (2 mL) was added propargyl bromide (80 mg, 0.672 mmol) and powdered cesium carbonate (219 mg, 0.672 mmol). The mixture was stirred under nitrogen at ambient temperature for 18 h. The reaction was diluted with water and extracted twice with ethyl acetate. The residue obtained from the combined organic extracts was purified by flash chromatography on silica gel eluting with 5:1 (v/v) hexane:ethyl acetate to afford the title compound (143 mg, 80%) as a white solid. TLC R1=0.19 (6:1 hexane:ethyl acetate). 1H NMR (300 MHz, CDCl3) δ1.38 (s, 9H), 2.30 (m, 1H), 4.69 (m, 2H), 4.96 (m, 2H), 5.66 (m, 1H), 7.28 (m, 3H), 7.39 (s, 5H), 7.48 (m, 1H). MS APCI, m/z=293 (M+1). LC/MS: 2.86 min.

Workup

  1. extractionextracted twice with ethyl acetate
  2. customThe residue obtained from the combined organic extracts
  3. customwas purified by flash chromatography on silica gel eluting with 5:1 (v/v) hexane

Sources & evidence

ORD record
ord-56ad840d6759486680dd2910362116fe
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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