tert-Butylsulfinamide, (S)-(-)- → HCID 87383933, compound

HRID 715802Notes

Reaction equation

HRID 715802 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:5][CH:4]=1)=O.[CH3:15][C:16]([S@@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17]>ClCCl.O.C(O[Ti](OCC)(OCC)OCC)C>[C:16]([S@@:19](/[N:21]=[CH:1]/[C:3]1[S:7][C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:5][CH:4]=1)=[O:20])([CH3:18])([CH3:17])[CH3:15]

Participants

6

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 21473735tert-Butyl 5-formylthiophene-2-carboxylate

Product 1

HCID 87383933HCID 87383933, compound

Reagents, catalysts & solvents 3

HCID 178477244HCID 178477244, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 5-formylthiophene-2-carboxylate (2 g, 9.42 mmol) and (S)-2-methylpropane-2-sulfinamide (1.370 g, 11.31 mmol) were dissolved in dichloromethane (100 ml). The mixture was chilled in an ice bath to which was added tetraethoxytitanium (8.7 ml, 41.5 mmol). The mixture was allowed to warm to room temperature overnight with stirring. The mixture was poured into a large Erlenmeyer flask with 200 mL dichloromethane and was diluted with 18 mL H2O. After vigorous stirring for 30 minutes the suspension was filtered through diatomaceous earth and the filtrate was concentrated. Purification using normal phase chromatography provided the title compound.

Workup

  1. temperatureThe mixture was chilled in an ice bath to which
  2. stirringAfter vigorous stirring for 30 minutes the suspension
  3. filtrationwas filtered through diatomaceous earth
  4. concentrationthe filtrate was concentrated
  5. customPurification

Sources & evidence

ORD record
ord-4bfb6c0e0810481a84c55d47a8e8442b
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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