Trifluoroacetic acid → 5-[4-(2-Aminoethyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one TFA Salt

HRID 660532Notes

Reaction equation

HRID 660532 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][C:19](=[O:21])[N:18]([CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[S:17]2(=[O:29])=[O:28])=[C:12]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:11]=1)(C)(C)C.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl>[OH:45][C:39]([C:41]([F:44])([F:43])[F:42])=[O:40].[NH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[S:17](=[O:29])(=[O:28])[N:18]([CH2:22][CH2:23][Si:24]([CH3:25])([CH3:26])[CH3:27])[C:19](=[O:21])[CH2:20]2)=[C:12]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68842331(2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-ethyl)-carbamic Acid Tert-butyl Ester

Product 1

HCID 866325725-[4-(2-Aminoethyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one TFA Salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-ethyl)-carbamic acid tert-butyl ester (1.5 g, 2.67 mmol) (from Example 59, step B) in 10 mL of CH2Cl2 is added TFA (4.0 mL). The mixture stirred for 30 min and then evaporated and azeotroped with toluene to afford the title compound as an orange foam.

Workup

  1. customevaporated
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-b895762ee5fe46a087da0940f34e2f41
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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