Iodoethane → N-(tert-Butoxy(hydroxy)methylidene)-O-ethylserine

HRID 2107868Notes

Reaction equation

HRID 2107868 reaction equation
[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C[O-].[Na+].[CH2:18](I)[CH3:19]>C1COCC1.CO>[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][O:4][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 6340Iodoethane3×HCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 10942334Sodium Methoxide3×

Product 1

HCID 15058451N-(tert-Butoxy(hydroxy)methylidene)-O-ethylserine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.94 g BocSer in 66 mL THF was added a solution of 1.47 g NaOMe in 2.6 mL MeOH, followed by 11.7 g EtI. After 15 minutes, more NaOMe (0.49 g) and EtI (2 mL) were added and the reaction was stirred at RT overnight. More NaOMe and EtI were added and the reaction was stirred for an additional 6 hours. The mixture was concentrated in vacuo, dissolved in 25 mL H2O and washed 2×25 mL ether. The aqueous phase was acidified with concentrated HCl and extracted 4×25 mL CH2Cl2. The combined extracts were dried over MgSO4, filtered and concentrated in vacuo to 0.34 g crude product which carried on. NMR (300 MHz, CDCl3), delta 1.19 (t, J=7 Hz, 3H), 1.46 (s, 9H), 3.53 (q, J=7 Hz, 2H), 4.43 (m, 1H).

Workup

  1. stirringthe reaction was stirred for an additional 6 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutiondissolved in 25 mL H2O
  4. washwashed 2×25 mL ether
  5. extractionextracted 4×25 mL CH2Cl2
  6. dry with materialThe combined extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to 0.34 g crude product which

Sources & evidence

ORD record
ord-51eaee3baba74dc9bdf961acb8253c23
Source dataset
uspto-grants-1990_06
Patent number
US04935405

Reaction notes

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