Hydrochloric Acid → O-[3-(allyloxycarbonyl)-benzyl]-N-(t-butoxycarbonyl)-L-serine

HRID 2414370Notes

Reaction equation

HRID 2414370 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].I[CH2:18][C:19]1[CH:20]=[C:21]([CH:28]=[CH:29][CH:30]=1)[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23].Cl>CN(C=O)C>[CH2:25]([O:24][C:22]([C:21]1[CH:20]=[C:19]([CH:30]=[CH:29][CH:28]=1)[CH2:18][O:13][CH2:12][C@@H:11]([C:14]([OH:16])=[O:15])[NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])=[O:23])[CH:26]=[CH2:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 11808802Allyl 3-iodomethylbenzoate

Product 1

HCID 54022019O-[3-(allyloxycarbonyl)-benzyl]-N-(t-butoxycarbonyl)-L-serine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (19.4 g, 60% in mineral oil, 484.4 mmol) is washed with dry hexanes (2×30 mL) to remove the mineral oil and then suspended in anhydrous DMF (330 mL). To this suspension a solution of N-(t-butoxycarbonyl)-L-serine (45.2 g, 220.2 mmol) in DMF (110 mL) at 0° C. is added dropwise with vigorous stirring. The mixture is stirred for an additional 5 minutes at 0° C., and then at room temperature for 30 minutes. The solution is cooled back to 0° C., and a solution of allyl 3-iodomethylbenzoate (66.6 g, 220.2 mmol) in DMF (110 mL) is added dropwise over 15 minutes. The mixture is then warmed to room temperature for 30 minutes. The reaction mixture is poured into ice water (2.2 L) and acidified to pH 2 with 1 N HCl (270 mL). The mixture is extracted with ether (1×600 mL, then 3×300 mL) and the combined ether extracts are then washed with water (5×200 ml) and then dried (MgSO4) and evaporated in vacuo to yield O-[3-(allyloxycarbonyl)-benzyl]-N-(t-butoxycarbonyl)-L-serine as a yellowish oil.

Workup

  1. customto remove the mineral oil
  2. waitat room temperature for 30 minutes
  3. temperatureThe solution is cooled back to 0° C.
  4. temperatureThe mixture is then warmed to room temperature for 30 minutes
  5. extractionThe mixture is extracted with ether (1×600 mL
  6. wash3×300 mL) and the combined ether extracts are then washed with water (5×200 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-80ffa4329d0346dfb8adddee08ca4641
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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