Water → HCID 90192598, compound

HRID 923464Notes

Reaction equation

HRID 923464 reaction equation
[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][CH2:7][C@:8]([NH:16][S@](C(C)(C)C)=O)([C:10]1[S:11][C:12]([CH3:15])=[CH:13][N:14]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].Cl.O1CCOCC1.C(N(CC)CC)C.O>O1CCCC1>[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][CH2:7][C@@:8]([C:10]1[S:11][C:12]([CH3:15])=[CH:13][N:14]=1)([NH2:16])[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 204431481,4-Dioxane hydrochlorideHCID 123560014HCID 123560014, compound

Product 1

HCID 90192598HCID 90192598, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 254 mg of (S)—N-[(2S)-1-{[tert-butyl (dimethyl)silyl]oxy}-2-(5-methyl-1,3-thiazol-2-yl)propan-2-yl]-2-methylpropane-2-sulfinamide in 6.9 ml of tetrahydrofuran (THF) was added 1.1 ml of a 4 M hydrogen chloride/1,4-dioxane solution, followed by stirring at room temperature for 4 hours. To the reaction mixture was added 0.62 ml of triethylamine, and water was then added thereto, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then evaporated under reduced pressure. To the obtained residue was added ethyl acetate and the insoluble materials were separated by filtration. The filtrate was concentrated under reduced pressure to obtain 185 mg of (2S)-1-{[tert-butyl (dimethyl)silyl]oxy}-2-(5-methyl-1,3-thiazol-2-yl)propan-2-amine.

Workup

  1. additionwas then added
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure
  5. additionTo the obtained residue was added ethyl acetate
  6. customthe insoluble materials were separated by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c4e658818b954760b7f6708275e8f5c6
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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