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1,4,5,6-Tetrahydropyrimidin-2-amine → (2S)-3-{4-[3-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-propoxy]-phenyl}-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester

HRID 1250871
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HRID 1250871 반응식
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@@H:16]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:11][CH:10]=1)C.[NH:36]1[CH2:41][CH2:40][CH2:39][N:38]=[C:37]1[NH2:42]>CN(C=O)C>[C:31]([O:30][C:28](=[O:29])[C@@H:16]([NH:17][S:18]([C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)(=[O:19])=[O:20])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4](=[O:3])[NH:42][C:37]2[NH:38][CH2:39][CH2:40][CH2:41][N:36]=2)=[CH:10][CH:11]=1)([CH3:34])([CH3:33])[CH3:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 699233804-{4-[(2S)-2-tert-Butoxycarbonyl-2-(toluene-4-sulfonylamino)-ethyl]-phenoxy}-butyric acid ethyl ester

생성물 1

HCID 57120024(2S)-3-{4-[3-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-propoxy]-phenyl}-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

295 mg of 4-{4-[(2S)-2-tert-Butoxycarbonyl-2-(toluene-4-sulfonylamino)-ethyl]-phenoxy}-butyric acid ethyl ester were dissolved in 15 ml of anhydrous DMF and 287 mg of 1,4,5,6-tetrahydropyrimidin-2-ylamine were added to the solution. The reaction mixture was stirred overnight at room temperature, and the solvent was removed in vacuo. The residue was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic phase was dried with anhydrous magnesium sulfate, filtered and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with a gradient of ethyl acetate/isopropanole/water (8/3/1 to 4/3/1). Yield 241 mg. MS: m/e=559.2 (M+H)+; 503.2.

후처리

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was chromatographed on silica gel eluting with a gradient of ethyl acetate/isopropanole/water (8/3/1 to 4/3/1)

출처 및 근거

ORD 기록
ord-64de7d22af2a42c89823253f5ca076a7
출처 데이터셋
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06340679B1

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