1-Hydroxybenzotriazole → HCID 57023450, compound

HRID 2289047Notes

Reaction equation

HRID 2289047 reaction equation
[CH3:1][N:2]1[CH2:9][CH2:8][CH2:7][C@H:3]1[C:4]([OH:6])=O.[NH2:10][C@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C>[C:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][C@H:11]([NH:10][C:4](=[O:6])[C@@H:3]2[CH2:7][CH2:8][CH2:9][N:2]2[CH3:1])[CH2:12]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 643474N-Methyl-L-prolineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57023450HCID 57023450, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-methyl-L-proline (600 mg) and (3S)-3-amino-1-(tert-butoxycarbonyl)pyrrolidine (758 mg) in anhydrous DMF (10 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (856 mg) and 1-hydroxybenzotriazole (550 mg) were added. The mixture was stirred overnight at room temperature. To the reaction mixture, ethyl acetate was added. The resulting mixture was washed with an aqueous solution of sodium carbonate, 15% saline and saturated saline, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column (ethyl acetate, 5% methanol/ethyl acetate, 10% methanol/ethyl acetate), whereby 1.11 g of (3S)-1-(tert-butoxycarbonyl)-3-(1-methyl-L-prolylamino)pyrrolidine were obtained.

Workup

  1. additionwere added
  2. washThe resulting mixture was washed with an aqueous solution of sodium carbonate, 15% saline and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue was purified by chromatography through a silica gel column (ethyl acetate, 5% methanol/ethyl acetate, 10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-8598906d8414472589b27eeb811386a5
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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