Benzyl Bromide → HCID 86754829, compound

HRID 1603654Notes

Reaction equation

HRID 1603654 reaction equation
[SH:1][C@H:2]1[N:5]([C:6](=[C:19]([CH3:21])[CH3:20])[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[O:8])[C:4](=[O:22])[C@@H:3]1[Br:23].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C.[Ag]>[CH2:24]([S:1][C@H:2]1[N:5]([C:6](=[C:19]([CH3:20])[CH3:21])[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[O:8])[C:4](=[O:22])[C@@H:3]1[Br:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 88477147HCID 88477147, compound

Product 1

HCID 86754829HCID 86754829, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of the silver salt of p-methoxybenzyl 2-[(3S, 4R)-4-mercapto-3-bromo-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (10 g, 20 mmol) in dry acetonitrile (100 ml) was treated with benzyl bromide (4 g, 24 mmol) and the resulting mixture refluxed for 30 mins. the reaction was cooled to room temperature, filtered, evaporated to dryness and the residue purified by flash chromatography using 1:1 ether:pentane as the eluting solvent. Evaporation of the appropriate fractions gave the product as a white solid (5.8 g, 59%), mp 70-72° C. 1H NMR δ (CDCl3)1.93 (3H, s, CH3), 2.23 (3H, s, CH3), 3.66 (1H, dd, J=2.9, 17.5 Hz, SCH2), 3.79 (3H, s, OCH3), 4.52 (1H, d, J=1.8 Hz, H3), 4.95 (1H, d, J=1.9 Hz, H4), 5.08 (2H, q, J=12.0 Hz, CO2CH2), 6.84-6.90 (2H, m, 2.6Ph--H), 7.13-7.31 (7H, m, 3,5Ph--H,Ph--H).

Workup

  1. temperaturethe resulting mixture refluxed for 30 mins
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customthe residue purified by flash chromatography
  5. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-f15e3363a9bb40f1a0ae3a6cbb637892
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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