Water → HCID 18318113, compound

HRID 1700258Notes

Reaction equation

HRID 1700258 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)([CH2:14]OS(C)(=O)=O)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[CH3:26][C:27]([S-:30])(C)[CH3:28].[Na+].O.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>CN(C=O)C.C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[CH:20]1([C:11]2([CH2:14][S:30][CH:27]([CH3:28])[CH3:26])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 5147913Sodium 2-methyl-2-propanethiolateHCID 22228407HCID 22228407, compound

Product 1

HCID 18318113HCID 18318113, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 1d (4 mmol) in DMF (25 mL) at rt was added sodium 2-methyl-2-propanethiolate (2 g, 20 mmol). The resultant suspension was stirred at rt for 18 hr then poured into water (75 mL) and extracted with EtOAc (2×75 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. Chromatography over silica eluting with 5:95 EtOAc/hexane furnished the N-protected product as a clear colourless oil. The N-Boc-protected sulfide was dissolved in CH2Cl2 (120 mL) and TFA (30 mL) was added. The resultant solution was stirred at rt for 1 hr. Volatiles were removed in vacuo to furnish the title compound as a clear colourless gum (1.34 g, 3.8 mmol). ESI-MS calcd for C15H29NS: 255; found 297 (M+H+MeCN).

Workup

  1. extractionextracted with EtOAc (2×75 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customChromatography over silica eluting with 5:95 EtOAc/hexane furnished the N-protected product as a clear colourless oil
  6. customVolatiles were removed in vacuo

Sources & evidence

ORD record
ord-9502c536d8ca47a1baf0bc74b5d8d849
Source dataset
uspto-grants-2002_02
Patent number
US06350760B1

Reaction notes

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