Diisopropylethylamine → HCID 56982734, compound

HRID 2289058Notes

Reaction equation

HRID 2289058 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27]([OH:29])=O)[CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.FC(F)(F)C(O)=O.[OH:48][CH:49]([CH2:59][NH:60][C:61]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][C:68]([N+:71]([O-:73])=[O:72])=[CH:67][CH:66]=1)=[O:62])[CH2:50][C:51]([NH:53][C@H:54]1[CH2:58][CH2:57][NH:56][CH2:55]1)=[O:52]>O1CCCC1>[OH:48][CH:49]([CH2:59][NH:60][C:61]([O:63][CH2:64][C:65]1[CH:66]=[CH:67][C:68]([N+:71]([O-:73])=[O:72])=[CH:69][CH:70]=1)=[O:62])[CH2:50][C:51]([NH:53][C@H:54]1[CH2:58][CH2:57][N:56]([C:27]([C@@H:11]2[CH2:10][C@H:9]([S:8][CH2:7][C:6]3[CH:30]=[CH:31][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:13][N:12]2[C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)=[O:15])=[O:29])[CH2:55]1)=[O:52]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 70098755HCID 70098755, compound

Product 1

HCID 56982734HCID 56982734, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

To a solution of (2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline (2.87 g) in anhydrous tetrahydrofuran (30 ml), N,N'-carbonyldiimidazole (1.25 g) was added, followed by stirring at 30° C. for one hour. To the reaction mixture, N,N-diisopropylethylamine (1.68 ml) and a solution of (3S)-3-[3-hydroxy-4-(4-nitrobenzyloxycarbonyl)aminobutanoylamino]pyrrolidine trifluoroacetate (3.19 g) in anhydrous tetrahydrofuran (30 ml) was added. The resulting mixture was allowed to stand overnight at room temperature. The reaction mixture was concentrated by evaporation under reduced pressure and ethyl acetate was added to the residue. The resulting mixture was washed successively with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography (dichloromethane-ethyl acetate-methanol) through a silica gel column, whereby 3.81 g of the title compound were obtained as an amorphous substance.

Workup

  1. waitto stand overnight at room temperature
  2. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure and ethyl acetate
  3. additionwas added to the residue
  4. washThe resulting mixture was washed successively with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was purified by chromatography (dichloromethane-ethyl acetate-methanol) through a silica gel column

Sources & evidence

ORD record
ord-1bec9c2c92fe42eeb5fd54c80f899dc8
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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