Carbon tetrabromide → HCID 178463279, compound

HRID 1527792Notes

Reaction equation

HRID 1527792 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:33])[C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([CH2:31][CH3:32])[C:16]2[C:17]([CH3:30])=[C:18]([CH:23]=[C:24]([C:26]#[C:27][CH2:28]O)[CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:54]>C(Cl)Cl>[Br:54][CH2:28][C:27]#[C:26][C:24]1[CH:25]=[C:16]([N:15]([C@H:12]2[CH2:13][CH2:14][C@H:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:33])[CH2:10][CH2:11]2)[CH2:31][CH3:32])[C:17]([CH3:30])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178463301HCID 178463301, compound

Product 1

HCID 178463279HCID 178463279, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-5-(3-hydroxyprop-1-yn-1-yl)-2-methylbenzoate (1.2 g, 2.62 mmol) in DCM (15 mL), PPh3 (1.37 g, 5.22 mmol) and CBr4 (1.7 g, 5.10 mmol) were added at 0° C. and reaction was stirred for 4 h at room temperature. On completion, reaction was quenched with ice water and extracted with dichloromethane. The combined organic layers were washed with water, dried, concentrated under reduced pressure. The crude material was purified by column chromatography to afford the title compound (0.5 g, 38.5% yield).

Workup

  1. customreaction
  2. customOn completion, reaction
  3. customwas quenched with ice water
  4. extractionextracted with dichloromethane
  5. washThe combined organic layers were washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-28339db572da4c8a8269b056ca551ff0
Source dataset
uspto-grants-2015_07
Patent number
US09089575B2

Reaction notes

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