Hydrochloric Acid → Ninhydrin

HRID 862876

反応式

HRID 862876 の反応式
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][C:6]([OH:8])=[O:7].[OH-:9].[Na+].[C:11](=[O:27])([O-])[O:12][C:13]1[CH:18]=[CH:17][C:16]([N+]([O-])=O)=[CH:15][C:14]=1[C:22](C)(C)C.Cl.[O:29]1[CH2:34][CH2:33][O:32]C[CH2:30]1>O>[C:11]([NH:1][CH2:2][CH2:3][NH:4][CH2:5][C:6]([OH:8])=[O:7])([O:12][C:13]([CH3:14])([CH3:18])[CH3:30])=[O:27].[CH:16]1[CH:15]=[C:14]2[C:22]([C:33]([OH:32])([OH:7])[C:34](=[O:29])[C:13]2=[CH:18][CH:17]=1)=[O:9]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2 回HCID 312751,4-Dioxane2 回HCID 428913N-(2-Aminoethyl)glycineHCID 67297514t-Butyl-p-nitrophenyl carbonate

生成物 2

HCID 10236NinhydrinHCID 9834393({2-[(Tert-butoxycarbonyl)amino]ethyl}amino)acetic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

The title compound was prepared by a modification of the procedure by Heimer et al. (Int. J Pept., 1984, 23, 203-211). N-(2-Aminoethyl)glycine (1, 3 g, 25.4 mmol) was dissolved in water (50 mL), dioxane (50 mL) was added, and the pH was adjusted to 11.2 with 2N sodium hydroxide. tert-Butyl-4-nitrophenyl carbonate (7.29 g, 30.5 mmol) was dissolved in dioxane (40 mL) and added dropwise over a period of 2 h, during which time the pH was maintained at 11.2 with 2N sodium hydroxide. The pH was adjusted periodically to 11.2 for three more hours and then the solution was allowed to stand overnight. The solution was cooled to 0° C. and the pH was carefully adjusted to 3.5 with 0.5M hydrochloric acid. The aqueous solution was washed with chloroform (3×200 mL), the pH adjusted to 9.5 with 2N sodium hydroxide and the solution was evaporated to dryness, in vacuo (14 mm Hg). The residue was extracted with DMF (25 mL+2×10 mL) and the extracts filtered to remove excess salt. This results in a solution of the title compound in about 60% yield and greater than 95% purity by tlc (system 1 and visualised with ninhydrin, Rf =0.3). The solution was used in the following preparations of BOC-aeg derivates without further purification.

後処理

  1. customThe title compound was prepared by a modification of the procedure by Heimer et al. (Int. J Pept., 1984, 23, 203-211)
  2. additionadded dropwise over a period of 2 h, during which time the pH
  3. washThe aqueous solution was washed with chloroform (3×200 mL)
  4. customthe solution was evaporated to dryness, in vacuo (14 mm Hg)
  5. extractionThe residue was extracted with DMF (25 mL+2×10 mL)
  6. filtrationthe extracts filtered
  7. customto remove excess salt

出典と根拠

ORDレコード
ord-91c0ab11250642498b89cb38409852b7
出典データセット
uspto-grants-1998_02
特許番号
US05719262

関連ノート

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