Dimethylformamide → HCID 10517849, compound

HRID 1052199Notes

Reaction equation

HRID 1052199 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:15]2[CH2:16][CH2:17][C:12]1([C:18]([OH:20])=O)[CH2:13][CH2:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.C(Cl)(=O)C([Cl:29])=O>O1CCCC1>[Cl:29][C:18]([C:12]12[N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH:15]([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10612438HCID 10612438, compound

Product 1

HCID 10517849HCID 10517849, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 7-[(benzyloxy)carbonyl]-7-azabicyclo[2.2.1]heptane-1-carboxylic acid (550 mg) produced above, N,N-dimethylformamide (0.02 mL) and tetrahydrofuran (10 mL) was added dropwise ethanedioyl dichloride (0.80 mL) at room temperature. The mixture was stirred at room temperature for 30 min, and the reaction system was concentrated under reduced pressure. To the residue was added a small amount of tetrahydrofuran, and the mixture was concentrated again under reduced pressure to give a crude product (2.0 mmol) of the title compound. The obtained crude product of the title compound was used for the next reaction without further purification.

Workup

  1. concentrationthe reaction system was concentrated under reduced pressure
  2. additionTo the residue was added a small amount of tetrahydrofuran
  3. concentrationthe mixture was concentrated again under reduced pressure

Sources & evidence

ORD record
ord-915d7a9da5e844d9abba58ee591ca85b
Source dataset
uspto-grants-2016_07
Patent number
US09388195B2

Reaction notes

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