(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline → HCID 86755550, compound

HRID 2289060Notes

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.[OH:32][C@@H:33]([C@@H:43]([NH:51][C:52]([O:54][CH2:55][C:56]1[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=1)=[O:53])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:34][C:35]([NH:37][C@H:38]1[CH2:42][CH2:41][NH:40][CH2:39]1)=[O:36]>O1CCCC1>[OH:32][C@@H:33]([C@@H:43]([NH:51][C:52]([O:54][CH2:55][C:56]1[CH:57]=[CH:58][C:59]([N+:62]([O-:64])=[O:63])=[CH:60][CH:61]=1)=[O:53])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:34][C:35]([NH:37][C@H:38]1[CH2:42][CH2:41][N:40]([C:27]([C@@H:11]2[CH2:10][C@H:9]([S:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:31][CH:30]=3)[CH2:13][N:12]2[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])=[O:29])[CH2:39]1)=[O:36]

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of (2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline (2.23 g) in anhydrous tetrahydrofuran (50 ml), N,N'-carbonyldiimidazole (0.97 g) was added, followed by stirring at 30° C. for 30 minutes. To the reaction mixture, a solution of (3S)-3-[(3R,4S)-3-hydroxy-4-(4-nitrobenzyloxycarbonyl)amino-5-phenylpentanoylamino]pyrrolidine (2.28 g) in anhydrous tetrahydrofuran (50 ml) was added. The resulting mixture was treated in a similar manner to that described in Referential Example 18-(1), whereby 2.14 g of the title compound were obtained as a powder.

Workup

additionThe resulting mixture was treated in a similar manner to that

Sources & evidence

ORD record: ord-b9110313d0824592bc03be6e3115fde4
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090802

Reaction notes

Loading…