Benzyl Bromide → HCID 67156552, compound

HRID 1035541Notes

Reaction equation

HRID 1035541 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([NH:30][C@H:31]([C:35]([O:37][CH3:38])=[O:36])[C@@H:32]([CH3:34])[OH:33])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOCC>[CH2:3]([O:33][C@H:32]([CH3:34])[C@@H:31]([C:35]([O:37][CH3:38])=[O:36])[NH:30][C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 11025190Methyl trityl-L-threoninate

Product 1

HCID 67156552HCID 67156552, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 250-mL, round-bottomed flask, under an atmosphere of N2, was charged with sodium hydride (60% oil dispersion, 772 mg, 19.3 mmol). The sodium hydride was washed with 3 portions of hexanes to remove the oil and then 8 mL of anhydrous DMF was added followed by benzyl bromide (3.38 mL, 28.4 mmol). The solution was cooled to 0° C. and then a solution of methyl N-trityl-L-threoninate (4.83 g, 12.9 mmol) dissolved in 12 mL of DMF was added dropwise via cannula over 5 minutes. After stirring for 2 hours, the reaction mixture was treated with saturated aqueous Na2CO3 solution and 200 mL of Et2O and the layers were separated. The organic portion was washed successively with H2O (5×100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 5-10% ethyl acetate/hexanes) gave 4.61 g of methyl O-benzyl-N-trityl-L-threoninate as a colorless syrup.

Workup

  1. washThe sodium hydride was washed with 3 portions of hexanes
  2. customto remove the oil
  3. addition8 mL of anhydrous DMF was added
  4. additionwas added dropwise via cannula over 5 minutes
  5. customthe layers were separated
  6. washThe organic portion was washed successively with H2O (5×100 mL) and brine (100 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b0b03c04ae5442088ad7e79cb15b836
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

Loading…