tert-Butyl isothiocyanate → HCID 131724470, compound

HRID 354256Notes

Reaction equation

HRID 354256 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C@@H:16]([OH:31])[C@@H:17]([NH2:30])[CH2:18][O:19][P:20]([O:23][CH2:24][CH2:25][N+:26]([CH3:29])([CH3:28])[CH3:27])([O-:22])=[O:21].[C:32]([N:36]=[C:37]=[S:38])(C)(C)[CH3:33].C(=O)(O)[O-].[Na+]>CO.O.ClCCl>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C@@H:16]([OH:31])[C@@H:17]([NH2:30])[CH2:18][O:19][P:20]([O:23][CH2:24][CH2:25][N+:26]([CH3:27])([CH3:29])[CH3:28])([O-:22])=[O:21].[CH2:32]([NH:36][C:37]([NH2:26])=[S:38])[CH3:33]

Participants

7

Reactant 3

HCID 11544tert-Butyl isothiocyanateHCID 516892Sodium BicarbonateHCID 98472901670-26-4

Product 1

HCID 131724470HCID 131724470, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

100 mg of sphingosylphosphorylcholine were dissolved in 10 ml methanol:water, 2:1, in a 25 ml Erlenmeyer flask. To the stirred solution were added 100 mg of tertiary butyl isothiocyanate. The solution was stirred for 10 min, then 2.5 ml of 1N sodium bicarbonate were added. The solution was left to stir for 48 hours, transferred to a separatory funnel and 80 ml dichloromethane, 30 ml methanol and 40 ml water were added. The organic phase was washed with 40 ml of water, then dried over MgSO4, filtered and evaporated to dryness. The compound was purified by preparative TLC using dichloromethane:methanol:water, 65:35:5 for development. The silica spot containing the product was viewed by an ultraviolet lamp, scraped and eluted with dichloromethane: methanol:water, 1:2:1, in a small column. Yield: 80 mg; M.S. Na+=574.

Workup

  1. waitThe solution was left
  2. stirringto stir for 48 hours
  3. customtransferred to a separatory funnel
  4. washThe organic phase was washed with 40 ml of water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe compound was purified by preparative TLC
  9. additionThe silica spot containing the product
  10. customwas viewed by an ultraviolet lamp
  11. washeluted with dichloromethane

Sources & evidence

ORD record
ord-0a38329aabb142389d01c0ba0d670b44
Source dataset
uspto-grants-2004_06
Patent number
US06756504B2

Reaction notes

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