Bromine → HCID 54357627, compound

HRID 1701669Notes

Reaction equation

HRID 1701669 reaction equation
[Br:1]Br.[O:3]([CH2:10][C:11]([NH:13][CH:14]1[CH2:17][N:16]([CH:18]([C:35]([CH3:37])=[CH2:36])[C:19]([O:21][CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[C:15]1=[O:38])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(=O)(O)[O-].[Na+]>O1CCCC1.O>[O:3]([CH2:10][C:11]([NH:13][CH:14]1[CH2:17][N:16]([C:18](=[C:35]([CH3:37])[CH2:36][Br:1])[C:19]([O:21][CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[C:15]1=[O:38])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 12416141HCID 12416141, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 54357627HCID 54357627, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4.1 ml of 1,5-diazabicyclo[5.4.0]undecene-5 (DBU) and 1.6 ml of bromine in 90 ml of tetrahydrofuran (THF) at -78° was added 4.36 g (9.0 mmol) of benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-3-methyl-3-butenoate in 20 ml of THF. The reaction mixture was placed in an ice bath and stirred for 20 minutes. Sodium bisulfite (3 g) in 30 ml of water was then added. After 10 min. the THF was removed under reduced pressure. Ethyl acetate was added to the resulting aqueous mixture. The organic layer was washed with dilute acid, sodium bicarbonate solution and brine (2X), dried, and evaporated in vacuo to provide 3.6 g (77%) of the title product: nmr (CDCl3) δ 2.13 and 2.28 (s, 3, CH3), 4.2 (m, 2, --CH2Br), 3.67 (m, 2, C4 --H), 4.97 (m, 1, C3 --H), 4.50 (s, 2, side chain CH2), and 7.2 (b, ArH).

Workup

  1. customThe reaction mixture was placed in an ice bath
  2. customAfter 10 min. the THF was removed under reduced pressure
  3. additionEthyl acetate was added to the resulting aqueous mixture
  4. washThe organic layer was washed
  5. additionwith dilute acid, sodium bicarbonate solution and brine (2X)
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-9df8f8d346964f53b799b3a837d92285
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

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