Triethylamine → N-(2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-ethyl)-C-cyclohexyl-methanesulfonamide

HRID 660647

Reaction equation

HRID 660647 reaction equation
OC(C(F)(F)F)=O.[NH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[S:21](=[O:23])(=[O:22])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:19](=[O:30])[CH2:18]2)=[C:13]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:12]=1.C(N(CC)CC)C.[CH:46]1([CH2:52][S:53](Cl)(=[O:55])=[O:54])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>C(Cl)Cl>[CH2:32]([O:31][C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][NH:8][S:53]([CH2:52][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)(=[O:55])=[O:54])[CH:16]=[CH:15][C:14]=1[N:17]1[CH2:18][C:19](=[O:30])[N:20]([CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[S:21]1(=[O:23])=[O:22])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3871475Cyclohexylmethane sulfonyl chlorideHCID 866325725-[4-(2-Aminoethyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one TFA Salt

Product 1

HCID 68997502N-(2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-ethyl)-C-cyclohexyl-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[4-(2-Aminoethyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one TFA salt (Example 67, step A) (0.49 g, 0.96 mmol) is dissolved in 5 mL of CH2Cl2 and triethylamine (0.27 mL, 1.92 mmol) is added. Cyclohexylmethyl sulfonyl chloride (0.19 g, 0.96 mmol) is then added and the reaction stirred for 1 h. The reaction mixture is concentrated and the residue is partitioned between EtOAc and 1N HCl and extracted with EtOAc. The combined organic layers are washed with sat. sodium bicarbonate and brine, dried over MgSO4 and concentrated to a yellow oil. The oil is purified by chromatography over silica (hexane/EtOAc gradient) to afford the title compound as an oil.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is partitioned between EtOAc and 1N HCl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers are washed with sat. sodium bicarbonate and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a yellow oil
  7. customThe oil is purified by chromatography over silica (hexane/EtOAc gradient)

Sources & evidence

ORD record
ord-a536dd7e9821469aaaaadfbefeb7930b
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Linked notes

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