Benzyl Bromide → methyl O-benzyl-N-trityl-L-threoninate

HRID 1663449Notes

Reaction equation

[C:1]([NH:20][C@H:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:22][OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[C:38]([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH2:30]([O:23][C@H:22]([CH3:38])[C@@H:21]([C:24]([O:26][CH3:27])=[O:25])[NH:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl N-trityl-L-serinate (136 g, 376 mmol) was dissolved in DMF (230 mL) and added dropwise to a stirred mixture of NaH (60% oil dispersion, 30.0 g, 752 mmol) and benzyl bromide (67.0 mL, 564 mmol) in 700 mL of DMF at 0° C. The resulting white suspension was stirred at 0° C. for 1 hour followed by the addition of saturated aqueous NaHCO3 solution. The reaction mixture was diluted with H2O and extracted repeatedly with Et2O. The combined organic layers were washed successively with H2O and brine, dried over MgSO4 and concentrated under reduced pressure to give 137 g of methyl O-benzyl-N-trityl-L-threoninate as a cloudy oil.

Workup

extractionextracted repeatedly with Et2O
washThe combined organic layers were washed successively with H2O and brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9538ac040b044ffda8525db96432e002
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034938B2

Reaction notes

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