Tert-Butanesulfinamide → HCID 87263023, compound

HRID 2365496Notes

Reaction equation

HRID 2365496 reaction equation
[CH3:1][C:2]1([CH3:28])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH:18]([NH:21][S:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[CH:19]=O)=[CH:11][CH:10]=2)[CH2:4][O:3]1.[C:29]([S:33]([NH2:35])=[O:34])([CH3:32])([CH3:31])[CH3:30]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH3:1][C:2]1([CH3:28])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH:18]([NH:21][S:22]([C:24]([CH3:26])([CH3:27])[CH3:25])=[O:23])/[CH:19]=[N:35]/[S:33]([C:29]([CH3:32])([CH3:31])[CH3:30])=[O:34])=[CH:11][CH:10]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 86641906HCID 86641906, compound

Product 1

HCID 87263023HCID 87263023, compound

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid {4-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-1-formyl-butyl}-amide in THF (20 ml) is added tert-butyl sulfinamide (323 mg, 2.7 mmol) followed by titanium ethoxide (1.0 ml, 4.8 mmol). The yellow solution formed is stirred at room temperature overnight. The solution is quenched with 1N NaOH (50 ml) and EtOAc (50 ml) and stirred for 30 minutes at room temperature. The resultant mixture is filtered through Celite™ (filter material) and the organic phase separated and dried (MgSO4). Concentration gives 2-Methyl-propane-2-sulfinic acid (4-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-1-{[(E)-2-methyl-propane-2-sulfinylimino]-methyl}-butyl)-amide as a mixture of diastereomers as a yellow oil; [M+H]+ 515.38

Workup

  1. customThe yellow solution formed
  2. customThe solution is quenched with 1N NaOH (50 ml) and EtOAc (50 ml)
  3. stirringstirred for 30 minutes at room temperature
  4. filtrationThe resultant mixture is filtered through Celite™ (filter material)
  5. customthe organic phase separated
  6. dry with materialdried (MgSO4)
  7. concentrationConcentration

Sources & evidence

ORD record
ord-89680ea08d8a42109774acddde5a4754
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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