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

HRID 629692
ノート
印刷プレビュー

反応式

HRID 629692 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c6c050d3adef4c7d97e4d290493d254e
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09315475B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート