1,2-Dichloroethane → HCID 57446125, compound

HRID 1803819Notes

Reaction equation

HRID 1803819 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 (8 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-20fdb496302b406b891d8d5eb3a65e57
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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