Trifluoroacetic acid → 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

HRID 660663Notes

Reaction equation

HRID 660663 reaction equation
C(OC([N:8]1[C@H:17](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:30][C:29](=[O:31])[N:28]([CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[S:27]3(=[O:39])=[O:38])=[C:22]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:21]=2)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:41]([O:40][C:22]1[CH:21]=[C:20](/[CH:19]=[CH:18]/[C@@H:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][NH:8]2)[CH:25]=[CH:24][C:23]=1[N:26]1[S:27](=[O:38])(=[O:39])[N:28]([CH2:32][CH2:33][Si:34]([CH3:35])([CH3:37])[CH3:36])[C:29](=[O:31])[CH2:30]1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68996827(S)-3-((E)-2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-vinyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-butyl Ester

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-((E)-2-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-vinyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.22 g, 0.32 mmol) in CH2Cl2 (8 mL) is added TFA (3 mL). After stirring at RT for 1.5 h, the mixture is concentrated under reduced pressure to give the title compound which is used directly in the next step.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d65604e2d908492184a970a60636970d
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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