Water → N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

HRID 980524

反応式

HRID 980524 の反応式
[C:1]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:18](N(CC)CC)C.COS(OC)(=O)=O.O>CN(C)C=O>[CH3:18][O:16][C:15](=[O:17])[C@H:12]([CH2:13][OH:14])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

参加物

6

反応物 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 100310N-(Benzyloxycarbonyl)-L-serine

生成物 1

HCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-CBZ-L-serine (25 g) was dissolved in 100 ml of dry N, N-dimethylformamide at 0° C. under argon. Triethylamine (2 e.g., 30 ml) and dimethylsulfate (20 ml) were added. The contents of the vessel were stirred overnight at room temperature and then poured into 500 ml of water and extracted with ethyl acetate (3×200 ml). The organic layer was washed with water and brine and dried with sodium sulfate. Rotary evaporation afforded an oil which crystallized after silica gel chromatography in pure ethyl ether. The structure of the product, N-CBZ-L-serine methyl ester, was confirmed by NMR spectroscopy.

後処理

  1. extractionextracted with ethyl acetate (3×200 ml)
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried with sodium sulfate
  4. customRotary evaporation
  5. customafforded an oil which
  6. customcrystallized after silica gel chromatography in pure ethyl ether

出典と根拠

ORDレコード
ord-1553a016876f4d24bed21628b5337efa
出典データセット
uspto-grants-1987_01
特許番号
US04638071

関連ノート

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