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

HRID 629692
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HRID 629692 반응식
[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
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c6c050d3adef4c7d97e4d290493d254e
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315475B2

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