Bromoacetyl bromide → HCID 70111628, compound

HRID 356217Notes

Reaction equation

HRID 356217 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[C:6]1([CH2:12][CH2:13][N:14]2[C:20](=[O:21])[C@H:19]3[CH2:22][CH2:23][CH2:24][C@H:18]3[NH:17][C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]2=3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])O.[Na+]>ClCCl>[Br:1][CH2:2][C:3]([N:17]1[C@@H:18]2[CH2:24][CH2:23][CH2:22][C@@H:19]2[C:20](=[O:21])[N:14]([CH2:13][CH2:12][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:15]2[CH:28]=[CH:27][CH:26]=[CH:25][C:16]1=2)=[O:4]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 70112258HCID 70112258, compound

Product 1

HCID 70111628HCID 70111628, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of bromoacetyl bromide (0.29 mL, 3.3 mmol) in dichloromethane (5 mL) was added dropwise a solution of (3aR*,10aS*)-9-(2-phenylethyl)-2,3,3a,4,9,10a- hexahydrobenzo [b]cyclopenta[e][1,4]diazepin-10(1H)-one (0.92 g, 3.0 mmol) in dichloromethane (5 mL). The solution was stirred for 3 hours at room temperature. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was separated, and the organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was purified by silica-gel column chromatography (hexane - ethyl acetate 5:1,then 1:1) to afford the desired product (924 mg, 72%). Oily product.

Workup

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  4. filtrationsubjected to filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe concentrate was purified by silica-gel column chromatography (hexane - ethyl acetate 5:1,then 1:1)

Sources & evidence

ORD record
ord-243005cf78f24782ad1dc34a8156b3ba
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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