1,2-Dichloroethane → HCID 57446125, compound

HRID 1170786Notes

Reaction equation

HRID 1170786 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]([CH2:7][NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.C(Cl)CCl.C1C=[CH:25][C:26]2[N:31](O)[N:30]=[N:29]C=2C=1.C1C[O:36]CC1>>[N:31]([CH2:26][C:25]([N:8]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:16][CH:15]=1)=[O:36])=[N+:30]=[N-:29]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 47002425HCID 47002425, compound

Product 1

HCID 57446125HCID 57446125, compoundYield 64%

Procedure

To a 25 mL round bottom flask containing 137 (0.307 g, 1.18 mmol) and azido acid (0.89 g, 1.77 mmol) in THF mL) was treated with EDC (0.362 g, 1.89 mmol), HOBt (0.255 g, 1.89 mmol) and TEA (0.83 mL, 5.9 mmol) at room temperature and was stirred for 12 h. The reaction was concentrated on silica and was purified over silica gel using EtOAc:Hexanes (2:1) as an eluent to afford 138 (0.259 g, 64%) as a yellow oil.

Workup

  1. concentrationThe reaction was concentrated on silica
  2. customwas purified over silica gel

Sources & evidence

ORD record
ord-621b991aca0b44ffbc6775d8da328fc4
Source dataset
uspto-grants-2010_11
Patent number
US07829063B2

Reaction notes

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