Hydrochloric Acid → Ninhydrin

HRID 50075

反応式

HRID 50075 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 2 N 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 2 N 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 0.5 M 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+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+2×10 mL)
  6. filtrationthe extracts filtered
  7. customto remove excess salt

出典と根拠

ORDレコード
ord-e459c34a7d944ed8ba1f67bbd66f298a
出典データセット
uspto-grants-2004_03
特許番号
US06710164B1

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