1,2-Dichloroethane → HCID 59552494, compound

HRID 1803816Notes

Reaction equation

HRID 1803816 reaction equation
[NH2:1][C@H:2]([CH2:8][S:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(Cl)CCl.C1C=[CH:30][C:31]2[N:36](O)[N:35]=[N:34]C=2C=1.C1C[O:41]CC1>>[N:36]([CH2:31][C:30]([NH:1][C@H:2]([CH2:8][S:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:41])=[N+:35]=[N-:34]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 59552687HCID 59552687, compound

Product 1

HCID 59552494HCID 59552494, compoundYield 89%

Procedure

To a 500 mL round bottom flask containing 131 (5.9 g, 17.38 mmol) and azido acid (2.13 g, 20.8 mmol) in THF (174 mL) was treated with EDC (5.33 g, 27.81 mmol), HOBt (3.75 g, 27.81 mmol) and TEA (12.2 mL, 86.9 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 (1:1) as an eluent to afford 132 (6.5 g, 89%) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-6fe0503a0f5c450bb1d6a3063b2a844d
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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