1,2-Dichloroethane → HCID 58928880, compound

HRID 853640Notes

Reaction equation

HRID 853640 reaction equation
FC(F)(F)C([O-])=O.[F:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][NH2+:17][CH2:16][C:15]2=[O:20])=[CH:11][CH:10]=1.[CH:23]([O:26][C:27]([C:29]1[C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=[CH:31][N:30]=1)=[O:28])([CH3:25])[CH3:24].C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH:23]([O:26][C:27]([C:29]1[C:34]([C:35]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:12]3[CH:21]=[CH:22][C:9]([F:8])=[CH:10][CH:11]=3)[C:15](=[O:20])[CH2:16]2)=[O:36])=[CH:33][CH:32]=[CH:31][N:30]=1)=[O:28])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 20750066HCID 20750066, compoundHCID 86593993HCID 86593993, compound

Product 1

HCID 58928880HCID 58928880, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 35 (1.46 g, 4.55 mmol) was dissolved in 20 mL of a 1:1 solution of CH2Cl2:DMF. To this solution was added 0.95 g (4.55 mmol) of 30, EDC (1.74 g, 9.10 mmol) and triethylamine (1.90 mL, 13.7 mmol). The solution was stirred at room temperature for 4 hours when the reaction was complete. The solution was diluted with CH2Cl2 and washed with water. The organic layer was subsequently washed with aq. saturated solution of NH4Cl and the solvent was removed. The yellow residue was purified by column chromatography using EtOAc-10% MeOH gradient to yield 1.8 g (100%) of the product 36 as a clear oil. EI MS (m/z) 400.5 [MH+], 422.3 [M+Na].

Workup

  1. washwashed with water
  2. washThe organic layer was subsequently washed with aq. saturated solution of NH4Cl
  3. customthe solvent was removed
  4. customThe yellow residue was purified by column chromatography

Sources & evidence

ORD record
ord-a3ac0aba39f34e5a94e9831dedc7602a
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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