1-Hydroxybenzotriazole → HCID 59620371, compound

HRID 2070138Notes

Reaction equation

HRID 2070138 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[C:6]([N:12]3[CH2:16][CH2:15][CH2:14][C:13]3=[O:17])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:18][C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[C:3]1=[O:24].O.[C:26]([O:30][C:31]([NH:33][C@@H:34]([C:39](O)=[O:40])[CH2:35][CH:36]([CH3:38])[CH3:37])=[O:32])([CH3:29])([CH3:28])[CH3:27].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[CH3:37][CH:36]([CH3:38])[CH2:35][C@@H:34]([NH:33][C:31](=[O:32])[O:30][C:26]([CH3:29])([CH3:28])[CH3:27])[C:39](=[O:40])[NH:1][CH:2]1[CH2:11][C:10]2[C:5](=[C:6]([N:12]3[CH2:16][CH2:15][CH2:14][C:13]3=[O:17])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:18][C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[C:3]1=[O:24]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724763BOC-D-LEU-OH H2OHCID 596203303-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 59620371HCID 59620371, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(−)-3-Amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one (500 mg) was dissolved in N,N-dimethylformaldehyde (5 mL), and to the solution were sequentially added N-tert-butoxycarbonyl-D-leucine monohydrate (382 mg), 1-hydroxybenzotriazole (207 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (294 mg) under cooling on ice, followed by stirring at room temperature for one hour. The resultant mixture was extracted with ethyl acetate and water, and the organic layer was sequentially washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, followed by drying over sodium sulfate. The solvent was evaporated under reduced pressure, and the thus-recovered residue was purified through silica gel column chromatography (chloroform:methanol=50:1), whereby the title compound (832 mg) was yielded.

Workup

  1. temperatureunder cooling on ice
  2. extractionThe resultant mixture was extracted with ethyl acetate and water
  3. washthe organic layer was sequentially washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialby drying over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe thus-recovered residue was purified through silica gel column chromatography (chloroform:methanol=50:1), whereby the title compound (832 mg)
  7. customwas yielded

Sources & evidence

ORD record
ord-cbcf347e60534f82a33c62822b57b792
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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