(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline → HCID 57039342, compound

HRID 2289059Notes

Reaction equation

HRID 2289059 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](O)=[O:28])[CH2:10]2)=[CH:5][CH:4]=1.[CH:32]1([CH2:38][C@H:39]([NH:51][C:52]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=2)=[O:53])[C@@H:40]([OH:50])[CH2:41][C:42]([NH:44][C@H:45]2[CH2:49][CH2:48][NH:47][CH2:46]2)=[O:43])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>O1CCCC1>[CH:32]1([CH2:38][C@H:39]([NH:51][C:52]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=2)=[O:53])[C@@H:40]([OH:50])[CH2:41][C:42]([NH:44][C@H:45]2[CH2:49][CH2:48][N:47]([C:27]([C@@H:11]3[CH2:10][C@H:9]([S:8][CH2:7][C:6]4[CH:30]=[CH:31][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[CH2:13][N:12]3[C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)=[O:15])=[O:28])[CH2:46]2)=[O:43])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 57108065HCID 57108065, compound

Product 1

HCID 57039342HCID 57039342, compound

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 (1.47 g) in anhydrous tetrahydrofuran (30 ml), N,N'-carbonyldiimidazole (0.59 g) was added, followed by stirring at 30° C. for one hour. To the reaction mixture, a solution of (3S)-3-[(3S,4S)-5-cyclohexyl-3-hydroxy-4-(4-nitrobenzyloxycarbonyl)aminopentanoylamino]pyrrolidine (1.38 g) in anhydrous tetrahydrofuran (30 ml) was added. The reaction mixture was treated in a similar manner to that described in Referential Example 18-(1), whereby 2.43 g of the title target compound were obtained as an amorphous substance.

Workup

  1. additionThe reaction mixture was treated in a similar manner to that
  2. customwhereby 2.43 g of the title target compound were obtained as an amorphous substance

Sources & evidence

ORD record
ord-a626451d9af34ec6890dbabbfb0fd1fc
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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