Diethyl Pyrocarbonate → HCID 178495709, 화합물

HRID 1009947노트

반응식

HRID 1009947 반응식
Cl.[CH3:2][O:3][CH2:4][C@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH2:26])=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1.C(N(CC)CC)C.[NH:34]1[C:38]2[CH:39]=[CH:40][C:41]([C:43](O)=[O:44])=[CH:42][C:37]=2[N:36]=[N:35]1.CCOC(OC(OCC)=O)=O>C1COCC1.O>[CH3:2][O:3][CH2:4][C@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH:26][C:43]([C:41]3[CH:40]=[CH:39][C:38]4[NH:34][N:35]=[N:36][C:37]=4[CH:42]=3)=[O:44])=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1

참가 물질

7

반응물 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 67150575(1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochlorideHCID 178524184HCID 178524184, 화합물

생성물 1

HCID 178495709HCID 178495709, 화합물수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution (5 ml) of (1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (200 mg, 0.480 mmol) in THF were added triethylamine (0.199 ml, 1.44 mmol), 1H-1,2,3-benzotriazole-5-carboxylic acid (78.3 mg, 0.480 mmol) and DEPC (0.079 ml, 0.528 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography using silica gel and eluted with hexane:ethyl acetate (1:1-1:9) to give the title compound (187 mg, 80%) as an amorphous form.

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. washeluted with hexane:ethyl acetate (1:1-1:9)

출처 및 근거

ORD 기록
ord-d5e803bed64b43ea9838bc73d551ed32
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973163B2

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