Cesium carbonate → HCID 59863937, compound

HRID 2267635Notes

Reaction equation

HRID 2267635 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].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[C:22]([O:21][C:20]([NH:19][C@@H:3]1[C:2](=[O:1])[N:8]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C@@H:4]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:26])([CH3:23])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 59863952HCID 59863952, compound

Product 1

HCID 59863937HCID 59863937, compoundYield 97%

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) (150 mg, 0.423 mmol) in dry DMF (4 mL) under nitrogen was added methyl bromoacetate (97 mg, 0.634 mmol) and powdered cesium carbonate (207 mg, 0.635 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 4:1 (v/v) hexane:ethyl acetate to afford the title compound (175 mg, 97%) as a white solid. TLC Rf=0.20 (4:1 hexane:ethyl acetate). 1H NMR (300 MHz, CDCl3) δ1.38 (s, 9H), 3.80 (s, 3H), 4.54 and 4.69 (AB quartet, 2H, J=17.1 Hz), 4.93 (m, 1H), 5.02 (m, 1H), 5.70 (d, 1H, J=7.0 Hz), 7.19-7.29 (m, 4H), 7.35-7.48 (m, 5H). MS APCI, m/z=327 (M-BOC). LC/MS: 2.76 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 4:1 (v/v) hexane

Sources & evidence

ORD record
ord-63fd8d46b13a452a999fb401486f48f0
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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