Pyrrolidine → HCID 13773263, compound

HRID 1651446Notes

Reaction equation

HRID 1651446 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:37]([N:39]1[N:43]=[C:42]([C:44]([CH3:47])([CH3:46])[CH3:45])[S:41][C@@H:40]1[C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49])=[O:38])[NH:17][C@H:18]([C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCC1>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:37]([N:39]1[N:43]=[C:42]([C:44]([CH3:47])([CH3:45])[CH3:46])[S:41][C@H:40]1[C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49])=[O:38])[NH:17][C@H:18]([C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 13773264HCID 13773264, compound

Product 1

HCID 13773263HCID 13773263, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the product of step (c) (2.lg) and pyrrolidine (1.6ml) in dry acetonitrile (60ml) was treated with crushed 3A molecular sieves and the mixture stirred at room temperature for 24 hours under nitrogen. The volatile materials were removed by evaporation and the SSS isomer separated from the more polar SSR isomer by flash chromatography. The SSS sub-title product (0.47g) was isolated as a clear oil.

Workup

  1. customThe volatile materials were removed by evaporation
  2. customthe SSS isomer separated from the more polar SSR isomer by flash chromatography

Sources & evidence

ORD record
ord-7f5b231f213f42f8ac56c966b3a6f4b9
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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