1,2-Dichloroethane → HCID 77442752, compound

HRID 409996Notes

Reaction equation

HRID 409996 reaction equation
[CH2:1](Cl)CCl.[CH:5]1[CH:6]=[CH:7][C:8]2[N:13](O)N=N[C:9]=2[CH:10]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([OH:23])=O)[CH:16]=1.NCC1C2[CH:29]([N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])CC2)CC1>C(Cl)Cl>[CH3:1][C:19]1[CH:18]=[C:17]([C:21]([NH:13][CH:8]2[CH:7]3[CH:29]([N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:5][CH2:6]3)[CH2:10][CH2:9]2)=[O:23])[CH:16]=[N:15][CH:20]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 938Nicotinic AcidHCID 757711-HydroxybenzotriazoleHCID 86762483HCID 86762483, compound

Product 1

HCID 77442752HCID 77442752, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100 mL round bottom flask was charged with a magnetic stirbar, EDC (3.8 g, 19.9 mmol), HOBT (4.1 g, 26.5 mmol), 5-methyl, 3-pyridine carboxylic acid (2.2 g, 15.9 mmol) and methylenechloride (35 mL). tert-Butyl 4-(aminomethyl)hexahydrocyclopenta[b]pyrrole-1(2H)-carboxylate (cis-isomer, racemic, >95% of one diastereomer, 3 g, 13.3 mmol) was added over 10 minutes and the reaction mixture was allowed to stir for 9 h at room temperature. The solvent was removed in vacuo, and the product was dissolved in chloroform and washed with water. The organic layer was dried with magnesium sulfate and solvent was removed in vacuo. The final compound was purified using reverse-phase HPLC to afford Compound 12. LC-MS, M+1=346.0

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe product was dissolved in chloroform
  3. washwashed with water
  4. dry with materialThe organic layer was dried with magnesium sulfate and solvent
  5. customwas removed in vacuo
  6. customThe final compound was purified

Sources & evidence

ORD record
ord-0a0c7c4e3393483388141dc348c5c9d9
Source dataset
uspto-grants-2014_06
Patent number
US08759539B2

Reaction notes

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