Triethylamine → 2-((E)-2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-vinyl)-piperidine-1-carboxylic Acid Tert-butyl Ester

HRID 660527Notes

Reaction equation

HRID 660527 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[CH:43]=[CH2:44])=[O:36])([CH3:33])([CH3:32])[CH3:31].C(N(CC)CC)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1P(C(C)(C)C)C(C)(C)C)(C)(C)C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1/[CH:43]=[CH:44]/[C:13]1[CH:12]=[CH:11][C:10]([N:16]2[CH2:17][C:18](=[O:29])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[S:20]2(=[O:22])=[O:21])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)=[O:36])([CH3:33])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14898394tert-butyl 2-Vinylpiperidine-1-carboxylateHCID 534414812,2'-Bis(DI-tert-butylphosphino)biphenylHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 688384762-((E)-2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-vinyl)-piperidine-1-carboxylic Acid Tert-butyl Ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (120 mg, 0.22 mmol) in MeCN (2 mL) is added 2-vinylpiperidine-1-carboxylic acid tert-butyl ester (51 mg, 0.242 mmol), triethylamine (33 mg, 0.33 mmol), 2,2′-bis(di-t-butylphosphino)biphenyl (2.6 mg) and Pd(OAc)2 (1.0 mg). The vessel is flushed with nitrogen and the mixture is stirred at 100° C. for 4 h. The mixture is partitioned between EtOAc/water and the organic phase is washed with water, brine and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using a gradient of EtOAc/hexane (5 to 25%) as eluent to give the title compound.

Workup

  1. customThe vessel is flushed with nitrogen
  2. customThe mixture is partitioned between EtOAc/water
  3. washthe organic phase is washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-849691edcd1e4b9fa4d0b6e2a48332dd
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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