Dichloromethane → HCID 66966216, compound

HRID 1711839Notes

Reaction equation

HRID 1711839 reaction equation
C([O:5][C:6](=[O:24])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[N:11][C:12]2[NH:21][C:20](=[O:22])[C@H:19]3[N:15]([CH2:16][CH2:17][CH2:18]3)[CH2:14][C:13]=2[CH:23]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:33]>CCOCC>[ClH:33].[O:22]=[C:20]1[C@H:19]2[N:15]([CH2:16][CH2:17][CH2:18]2)[CH2:14][C:13]2[CH:23]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:24])=[O:5])[CH:10]=[N:11][C:12]=2[NH:21]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66966846HCID 66966846, compound

Product 1

HCID 66966216HCID 66966216, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (S)-(E)-3-(10-oxo-2,3,4,9,10,10a-hexahydro-1H-3a,8,9-triaza-benzo[f]azulen-6-yl)acrylic acid tert-butyl ester (0.65 g, 1.97 mmol) in CH2Cl2 (7 mL) was treated with TFA (7 mL). After stirring at room temperature for 30 min, the clear tan solution was concentrated in vacuo. The resulting oil was treated with anhydrous dioxane (20 mL of a 4.0 M solution in dioxane, 80 mmol). The resulting mixture was sonicated for 5 min, stirred under N2 for 5 min and diluted with Et2O. The solid was isolated by filtration, suspended in Et2O, concentrated to dryness, and dried under vacuum overnight to give the title compound (0.60 g, 88%) as an off-white solid: MS (ESI) m/e 274 (M+H)+.

Workup

  1. concentrationthe clear tan solution was concentrated in vacuo
  2. additionThe resulting oil was treated with anhydrous dioxane (20 mL of a 4.0 M solution in dioxane, 80 mmol)
  3. customThe resulting mixture was sonicated for 5 min
  4. stirringstirred under N2 for 5 min
  5. additiondiluted with Et2O
  6. customThe solid was isolated by filtration
  7. concentrationconcentrated to dryness
  8. customdried under vacuum overnight

Sources & evidence

ORD record
ord-e5cc84bd66324002ae9afbab4d43840f
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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