Propylamine → HCID 68520809, compound

HRID 644949Notes

Reaction equation

HRID 644949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:12]([C:13]([N:15]3[CH2:20][CH2:19][C:18]([CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)([CH2:21][N:22]4[C:26]([CH3:28])([CH3:27])[CH2:25][O:24][C:23]4=[O:29])[CH2:17][CH2:16]3)=[O:14])[CH2:11][C@@H:10]([N:36]([CH3:52])S(C3C=CC([N+]([O-])=O)=CC=3[N+]([O-])=O)(=O)=O)[CH2:9]2)=[CH:4][CH:3]=1.C(N)CC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:9][C@H:10]([NH:36][CH3:52])[CH2:11][C@H:12]2[C:13]([N:15]2[CH2:20][CH2:19][C:18]([CH2:21][N:22]3[C:26]([CH3:27])([CH3:28])[CH2:25][O:24][C:23]3=[O:29])([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[CH2:17][CH2:16]2)=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 86602836HCID 86602836, compound

Product 1

HCID 68520809HCID 68520809, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10 mL round bottom flask equipped with a magnetic stir bar was charged with 0.184 g (0.24 mmol) of the product of Step G dissolved in 2 mL of methylene chloride and the reaction mixture was stirred at room temperature. Propylamine (50 μL, 0.49 mmol) was added via syringe and the reaction mixture developed an intense yellow color. Stirring was continued an additional 15 min, at which point TLC analysis (75% ethyl acetate-hexanes) revealed complete reaction of the starting material. The reaction mixture was concentrated in vacuo, and the residue was applied to two 1000 micron preparative TLC plates. Elution of the plates with a mixture of methylene chloride-methanol-14.8 N aqueous ammonium hydroxide (90:9:1) followed by recovery of the product band from the silica gel afforded 0.040 g of the title compound.

Workup

  1. customA 10 mL round bottom flask equipped with a magnetic stir bar
  2. stirringStirring
  3. customreaction of the starting material
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. washElution of the plates
  6. additionwith a mixture of methylene chloride-methanol-14.8 N aqueous ammonium hydroxide (90:9:1)

Sources & evidence

ORD record
ord-b2d1a6fe9bf74304b1ee47dcc71e58de
Source dataset
uspto-grants-2010_04
Patent number
US07700778B2

Reaction notes

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