Dicyclohexylcarbodiimide → HCID 131726110, compound

HRID 130301Notes

Reaction equation

HRID 130301 reaction equation
[Br:1][CH:2]([CH3:6])C(O)=O.C1CCC(N=[C:14]=[N:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)CC1.N[AsH:23](=[O:30])C1C=CC=CC=1.Cl.CC[O:34]CC>ClCCl.CN(C=O)C.C(N(CC)CC)C>[Br:1][CH2:2][CH2:6][C:14]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([AsH2:23]=[O:30])=[CH:20][CH:21]=1)=[O:34]

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 117292-Bromopropionic acidHCID 10953452Ether hydrochlorideHCID 131726111HCID 131726111, compound2×

Product 1

HCID 131726110HCID 131726110, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Bromopropionic acid anhydride [formed by reacting bromopropionic acid (1.66 g, 10.86 mmol) with DCC (1.12 g, 5.43 mmol) in 20 ml anhydrous dichloromethane for 15 minutes at 25° C., and filtering off the solid that precipitated] was added to a solution of aminophenylarsineoxide (1 g, 5.43 mmol, synthesized according to published protocol) in 10 ml DMF, and allowed to stir overnight. The amino phenylarsineoxide was rendered soluble by adding to it 10.86 mmol HCl/ether followed by neutralization with triethylamine and filtering the away the solid that formed. The solution was quenched with 20 ml water, and filtered to remove solids. The filtrate was evaporated to an oil, and purified via flash chromatography. In later preparations, 3-bromopropionyl chloride was used instead of the anhydride.

Workup

  1. customfor 15 minutes
  2. customat 25° C.
  3. filtrationfiltering off the solid
  4. customthat precipitated]
  5. filtrationfiltering the away the solid
  6. customthat formed
  7. customThe solution was quenched with 20 ml water
  8. filtrationfiltered
  9. customto remove solids
  10. customThe filtrate was evaporated to an oil
  11. custompurified via flash chromatography

Sources & evidence

ORD record
ord-2edc4b75532447c68dc277e09ecc7530
Source dataset
uspto-grants-2008_06
Patent number
US07381572B2

Reaction notes

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