Water → methyl N-benzyl-O-[tert-butyl(dimethyl)silyl]-D-serinate

HRID 629692Notes

Reaction equation

HRID 629692 reaction equation
[CH2:1]([NH:8][C@@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([NH:8][C@@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][O:11][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11063677(R)-Methyl 2-(benzylamino)-3-hydroxypropanoate

Product 1

HCID 15456533methyl N-benzyl-O-[tert-butyl(dimethyl)silyl]-D-serinate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To methyl N-benzyl-D-serinate (1 eq.) in CH2Cl2 (0.3 M) at rt were added triethylamine (1 eq) and DMAP (0.05 eq). The reaction mixture was cooled to 0° C. and TBS-Cl (1.1 eq) was added. The reaction mixture was stirred at rt for 16 hrs, water was added and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with saturated aqueous NH4Cl, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2
  2. washThe combined organic layers were washed with saturated aqueous NH4Cl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c6c050d3adef4c7d97e4d290493d254e
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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