1-Hydroxybenzotriazole → HCID 56998234, compound

HRID 2289083Notes

Reaction equation

HRID 2289083 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([C@H:23]1[CH2:27][CH2:26][NH:25][CH2:24]1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11].C(N(CC)C(C)C)(C)C.[C:37]([CH2:40][CH:41]([C@@H:43]1[CH2:47][C@H:46]([S:48][CH2:49][C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)[CH2:45][N:44]1[C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][C:65]([N+:68]([O-:70])=[O:69])=[CH:64][CH:63]=1)=[O:59])[OH:42])(O)=[O:38].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[OH:42][CH:41]([C@@H:43]1[CH2:47][C@H:46]([S:48][CH2:49][C:50]2[CH:51]=[CH:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=2)[CH2:45][N:44]1[C:58]([O:60][CH2:61][C:62]1[CH:63]=[CH:64][C:65]([N+:68]([O-:70])=[O:69])=[CH:66][CH:67]=1)=[O:59])[CH2:40][C:37]([N:25]1[CH2:26][CH2:27][C@H:23]([N:9]([CH3:8])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:24]1)=[O:38]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57256052HCID 57256052, compoundHCID 70273891HCID 70273891, compound

Product 1

HCID 56998234HCID 56998234, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

In dimethylformamide (5 ml), (3S)-3-[N-methyl-N-(4-nitrobenzyloxycarbonyl)amino]pyrrolidine trifluoroacetate (400.9 mg) was dissolved. To the solution, N,N-diisopropylethylamine (0.444 ml) and a solution of (2S,4S)-2-(2-carboxy-1-hydroxyethyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.5 g) in dimethylformamide (5 ml), were added at room temperature. To the resulting mixture, 1-hydroxybenzotriazole (151.5 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (273.5 mg) and water (1 ml) were added successively and the mixture was stirred overnight at the same temperature. The reaction mixture was concentrated by evaporation under reduced pressure. Ethyl acetate was then added to the residue. The resulting mixture was washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column (ethyl acetate methanol=50:1), whereby (2S,4S)-2-[1-hydroxy-2-[(3S)-3-[N-methyl-N-(4-nitrobenzyloxycarbonyl)amino]pyrrolidin-1-ylcarbonyl]ethyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (523.5 mg) was obtained

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  2. additionEthyl acetate was then added to the residue
  3. washThe resulting mixture was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by chromatography through a silica gel column (ethyl acetate methanol=50:1)

Sources & evidence

ORD record
ord-d9832ee8544743d39c2c101ea7d78af2
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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