Hydrochloric Acid → [3-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester

HRID 1069648노트

반응식

HRID 1069648 반응식
[CH3:1][O:2][P:3]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:15]=[C:14]2[CH2:27][C:28]([O:30]CC)=O)(=[O:6])[O:4][CH3:5].[Al]([NH2:36])(C)C.O.Cl>C1(C)C=CC=CC=1.C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:1][O:2][P:3]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:15]=[C:14]2[CH2:27][C:28]([NH2:36])=[O:30])(=[O:6])[O:4][CH3:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10813793[3-[[3-(2-ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl esterHCID 16689643Aminodimethyl aluminium

생성물 1

HCID 10550559[3-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester수율 80%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 160055Benzene, mixed with toluene, dealkylation product용매

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온도
50 °C

실험 절차

[3-[[3-(2-Ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester (590 mg, 1.3 mmol) was dissolved in 40 mL of toluene and 10 mL of 0.67M (CH3)2AlNH2 in benzene/toluene were added. The mixture was heated at 50° C. for 3.25 hours and water and 1N HCl added. The mixture was extracted with a large volume of ethyl acetate and the organic layer was washed with brine, dried (Na2SO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with a gradient, 1% MeOH/methylene chloride→4% MeOH/methylene chloride, to give 450 mg (80% yield) of [3-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester.

후처리

  1. extractionThe mixture was extracted with a large volume of ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was chromatographed on silica gel eluting with a gradient, 1% MeOH/methylene chloride→4% MeOH/methylene chloride

출처 및 근거

ORD 기록
ord-182ae11f6e2047e297a9af07711b2189
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06252084B1

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