Hydrochloric Acid → Ninhydrin

HRID 862876

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HRID 862876 반응식
[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]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2회HCID 312751,4-Dioxane2회HCID 428913N-(2-Aminoethyl)glycineHCID 67297514t-Butyl-p-nitrophenyl carbonate

생성물 2

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

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-91c0ab11250642498b89cb38409852b7
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719262

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