Pyrrolidine → HCID 68578725, compound

HRID 886950Notes

Reaction equation

HRID 886950 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([OH:21])=O)[C:12]=2[O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=N1.N1CCCC1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[N:25]1([C:19]([C:18]2[C:12]3[O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:14][C:13]=3[CH:15]=[CH:16][CH:17]=2)=[O:21])[CH2:26][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 685781121055880-94-8

Product 1

HCID 68578725HCID 68578725, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(tert-butoxycarbonyl)-2,3,4,5-tetrahydro-1,4-benzoxazepine-9-carboxylic acid (40.0 mg, 0.136 mmol), 1-hydroxybenzotriazole (18.4 mg, 0.136 mmol) and pyrrolidine (0.017 ml, 0.204 mmol) in DMF (1 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (52.2 mg, 0.272 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the desired product (42.0 mg, 89.2%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-762225e1b9684489b05b6691c8cc88d1
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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