5-Chloro-salicylaldehyde → 2-(3-{[(5-Chloro-2-hydroxy-benzyl)-((S)-1-dimethylaminomethyl-3,3-dimethyl-butyl)-amino]-methyl}-benzyl)-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide

HRID 1879477Notes

Reaction equation

HRID 1879477 reaction equation
[CH3:1][C@@H:2]1[C@@H:7]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[N:12]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH:26][C@H:27]([CH2:33][N:34]([CH3:36])[CH3:35])[CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:20]=2)=[O:10])[CH2:6][C@H:5]2[CH2:37][C@@H:3]1[C:4]2([CH3:39])[CH3:38].[Cl:40][C:41]1[CH:42]=[CH:43][C:44]([OH:49])=[C:45]([CH:48]=1)[CH:46]=O>>[CH3:1][C@@H:2]1[C@@H:7]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[N:12]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]([CH2:46][C:45]3[CH:48]=[C:41]([Cl:40])[CH:42]=[CH:43][C:44]=3[OH:49])[C@H:27]([CH2:33][N:34]([CH3:35])[CH3:36])[CH2:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH:20]=2)=[O:10])[CH2:6][C@H:5]2[CH2:37][C@@H:3]1[C:4]2([CH3:38])[CH3:39]

Participants

3

Reactant 2

HCID 124815-Chloro-salicylaldehydeHCID 67153255HCID 67153255, compound2×

Product 1

HCID 529532272-(3-{[(5-Chloro-2-hydroxy-benzyl)-((S)-1-dimethylaminomethyl-3,3-dimethyl-butyl)-amino]-methyl}-benzyl)-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amideYield 18%

Procedure

Using Method A, 2-{3-[((S)-1-Dimethylaminomethyl-3,3-dimethyl-butylamino)methyl]-benzyl}-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide (Intermediate 6, 0.200 g, 0.360 mmol) and 5-chloro-2-hydroxy-benzaldehyde (available from Aldrich; 0.066 g, 0.430 mmol) were reacted to form 2-(3-{[(5-Chloro-2-hydroxy-benzyl)-((S)-1-dimethylaminomethyl-3,3-dimethyl-butyl)-amino]-methyl}-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide (0.0450 g, 18%). Mass spectrum: m/Z: 701.5 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1be4fc7b57ec40dc9e7a34d2436572c8
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

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