1-Hydroxybenzotriazole → HCID 57128097, compound

HRID 1601021Notes

Reaction equation

HRID 1601021 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:20]([OH:22])=O)[CH2:3]1.Cl.[CH3:24][N:25]([CH2:39][C@H:40]1[CH2:44][CH2:43][NH:42][CH2:41]1)[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:27].C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[O:8])[C@H:4]([C:20]([N:42]2[CH2:43][CH2:44][C@H:40]([CH2:39][N:25]([CH3:24])[C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])[CH2:41]2)=[O:22])[CH2:3]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10566895trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 70100666HCID 70100666, compound

Product 1

HCID 57128097HCID 57128097, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,4R)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)proline (4.65 g) in anhydrous dimethylformamide (60 ml), (3S)-3-[N-methyl-N-(4-nitrobenzyloxycarbonyl)aminomethyl]pyrrolidine hydrochloride (4.95 g), diisopropylethylamine (5.23 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.03 g) and 1-hydroxybenzotriazole (2.23 g) were added. The resulting mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated by evaporation under reduced pressure. The residue was dissolved in ethyl acetate. The resulting solution was washed with water and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was subjected to chromatography through a silica gel column. From the fractions eluted with ethyl acetate/methanol=9/1, (2S,4R)-4-hydroxy-2-[(3S)-3-[N-methyl-N-(4-nitrobenzyloxycarbonyl)aminomethyl]pyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (8.70 g) was obtained as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe resulting solution was washed with water
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. washFrom the fractions eluted with ethyl acetate/methanol=9/1

Sources & evidence

ORD record
ord-9dbdf6ffac0b4c3381768545c43b3d61
Source dataset
uspto-grants-1999_11
Patent number
US05977097

Reaction notes

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