Triethylamine → 5-{2-Benzyloxy-4-[(E)-2-((S)-2-methanesulfonyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 660664Notes

Reaction equation

HRID 660664 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C@@H:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][NH:18]2)[CH:12]=[CH:11][C:10]=1[N:27]1[S:31](=[O:33])(=[O:32])[N:30]([CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:29](=[O:40])[CH2:28]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:48][S:49](Cl)(=[O:51])=[O:50]>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C@@H:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][N:18]2[S:49]([CH3:48])(=[O:51])=[O:50])[CH:12]=[CH:11][C:10]=1[N:27]1[S:31](=[O:32])(=[O:33])[N:30]([CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])[C:29](=[O:40])[CH2:28]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 688396835-{2-Benzyloxy-4-[(E)-(S)-2-(1,2,3,4-tetrahydroisoquinolin-3-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 688389915-{2-Benzyloxy-4-[(E)-2-((S)-2-methanesulfonyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-{2-benzyloxy-4-[(E)-(S)-2-(1,2,3,4-tetrahydroisoquinolin-3-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (0.12 g, 0.21 mmol) in CH2Cl2 (2 mL) is added triethylamine (0.15 mL, 1.0 mmol), followed by methanesulfonyl chloride (0.020 mL, 0.25 mmol). The mixture is stirred at RT for 1.5 h then is diluted with EtOAc (15 mL) and washed with 1N HCl (2×15 mL) and brine (1×15 mL). The organic layer is dried over Na2SO4, concentrated in vacuo and used directly in the next step without further purification.

Workup

  1. washwashed with 1N HCl (2×15 mL) and brine (1×15 mL)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customused directly in the next step without further purification

Sources & evidence

ORD record
ord-4983a2b071304dcea47cc537c6e61e9f
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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