Succinic anhydride → HCID 89668745, compound

HRID 1482375Notes

Reaction equation

HRID 1482375 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:22][C@H:21]([OH:23])[CH2:20][C@H:19]3[C:24](=[O:55])[NH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][C:32]([C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=3)([C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:56]1(=[O:62])[O:61][C:59](=[O:60])[CH2:58][CH2:57]1>C(#N)C>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([C:32]([C:47]2[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][NH:25][C:24]([C@H:19]2[N:18]([C:16]([O:15][CH2:14][CH:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)=[O:17])[CH2:22][C@H:21]([O:23][C:56](=[O:62])[CH2:57][CH2:58][C:59]([OH:61])=[O:60])[CH2:20]2)=[O:55])=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 89668762HCID 89668762, compound2×

Product 1

HCID 89668745HCID 89668745, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2S,4R)-2-(2-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethoxy}-ethylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (Compound 73) (1.00 g, 1.35 mmol), succinic anhydride (192 mg, 2.02 mmol) and N,N-dimethylaminopyridine (246 mg, 2.02 mmol) were dissolved in acetonitrile (3.0 mL), and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was purified by reverse-phase silica (0.1% ammonium acetate, H2O, CH3OH, gradient) to afford the title compound (Compound 74) (349 mg, 31%) as a colorless amorphous.

Workup

  1. customThe reaction solution was purified by reverse-phase silica (0.1% ammonium acetate, H2O, CH3OH, gradient)

Sources & evidence

ORD record
ord-e0149e6ed4114735ab46cd7351efab24
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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