1,2-Dichloroethane → HCID 11813822, compound

HRID 751754Notes

Reaction equation

HRID 751754 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12](C(O)=O)[CH2:13][O:14][C:15]([C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:46])[C@@H:23]([NH:25][C:26]([C@@H:28]([N:30]([CH3:45])[C:31]([C@@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1[C:38](OC(C)(C)C)=[O:39])=[O:32])[CH3:29])=[O:27])[CH3:24])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC1C(O)=C(F)C(F)=C(F)C=1F.C(Cl)CCl>ClCCl>[CH3:24][C@@H:23]1[NH:25][C:26](=[O:27])[C@H:28]([CH3:29])[N:30]([CH3:45])[C:31](=[O:32])[C@H:33]2[N:34]([CH2:35][CH2:36][CH2:37]2)[C:38](=[O:39])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][O:14][C:15](=[O:16])[C@H:17]2[N:18]([CH2:19][CH2:20][CH2:21]2)[C:22]1=[O:46]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 11017897HCID 11017897, compound

Product 1

HCID 11813822HCID 11813822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

109.0 g (158 mmol) of the carboxylic acid from example 9A and 116.4 g (632 mmol) of pentafluorophenol are dissolved in 1000 ml of anhydrous dichloromethane, cooled to −20° C. and 39.4 g (205 mmol) of EDC are introduced. The reaction mixture is stirred overnight with slow warming to RT. The solvent is removed in vacuo and the residue is treated with hydrogen chloride in dioxane (600 ml) with ice cooling. The mixture is stirred at RT for 3 h, the solvent is removed in vacuo and the residue is taken up three times using toluene and again concentrated to dryness. The residue is divided into thirds and each part is treated as follows: The intermediate product is taken up in dichloromethane (900 ml) and introduced with a flow rate of 0.8 ml/min at RT into a vigorously stirred 2-phase mixture of 1.5 l of aqueous sodium hydrogencarbonate solution and 5 l of dichloromethane and stirred for about 2 h. The organic phase is separated off, the aqueous phase is extracted three times with 500 ml each of dichloromethane, and the combined organic phases are dried over sodium sulfate, filtered and concentrated to dryness.

Workup

  1. temperaturewith slow warming to RT
  2. customThe solvent is removed in vacuo
  3. additionthe residue is treated with hydrogen chloride in dioxane (600 ml) with ice cooling
  4. stirringThe mixture is stirred at RT for 3 h
  5. customthe solvent is removed in vacuo
  6. concentrationagain concentrated to dryness
  7. additioneach part is treated
  8. additionintroduced with a flow rate of 0.8 ml/min at RT into a vigorously stirred 2-phase mixture of 1.5 l of aqueous sodium hydrogencarbonate solution and 5 l of dichloromethane
  9. stirringstirred for about 2 h
  10. customThe organic phase is separated off
  11. extractionthe aqueous phase is extracted three times with 500 ml each of dichloromethane
  12. dry with materialthe combined organic phases are dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8dbdf1bdfb804f8cb1df32639fe8d4f7
Source dataset
uspto-grants-2008_07
Patent number
US07405201B2

Reaction notes

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