Dimethylformamide → racemic (2'S,3S,4'R)-1'-(aminocarbonyl-methyl)-6-chloro-2'-(3-chlorophenyl)-4'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1206841Notes

Reaction equation

HRID 1206841 reaction equation
[Br:41][CH2:42][C:43](=[O:44])[NH2:45].[C:46](=[O:47])([O-:48])[O-:49].[CH3:1][O:2][CH:3]([Si:4]([CH3:5])([CH3:6])[CH3:7])[CH3:8].[Cl:64][CH2:65][Cl:66].[Cl:9][c:10]1[cH:11][cH:12][c:13]2[c:17]([cH:18]1)[NH:16][C:15](=[O:19])[C:14]21[CH:20]([c:34]2[cH:35][c:36]([Cl:40])[cH:37][cH:38][cH:39]2)[NH:21][C:22](=[O:33])[CH2:23][CH:24]1[c:25]1[c:26]([CH3:32])[cH:27][cH:28][c:29]([F:31])[cH:30]1.[Cs+:50].[Cs+:51].[O:52]=[CH:53][N:54]([CH3:55])[CH3:56].[OH:57][C:58]([C:59]([F:60])([F:61])[F:62])=[O:63]>>[Cl:9][c:10]1[cH:11][cH:12][c:13]2[c:17]([cH:18]1)[NH:16][C:15](=[O:19])[C:14]21[CH:20]([c:34]2[cH:35][c:36]([Cl:40])[cH:37][cH:38][cH:39]2)[N:21]([CH2:42][C:43](=[O:44])[NH2:45])[C:22](=[O:33])[CH2:23][CH:24]1[c:25]1[c:26]([CH3:32])[cH:27][cH:28][c:29]([F:31])[cH:30]1

Participants

9

Reactant 8

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 19660Carbonate IonHCID 696322-BromoacetamideHCID 104967Cesium cation2×HCID 22400412(1-Methoxyethyl)(trimethyl)silaneHCID 76568090racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 76568085racemic (2'S,3S,4'R)-1'-(aminocarbonyl-methyl)-6-chloro-2'-(3-chlorophenyl)-4'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Sources & evidence

ORD record
ord-83da5967d993470b96631b85418e6a25
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (5/10)

Reaction notes

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