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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Acetic Acid → (1R,2S,3R)-3-[6'-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-3,4,5,6-tetrahydro-2H-1,2'-bipyridinyl-4-ylamino]cyclopentane-1,2-diol

HRID 2175099
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HRID 2175099 반응식
[NH2:1][C@@H:2]1[CH2:6][CH2:5][C@@H:4]([OH:7])[C@H:3]1[OH:8].CCN(C(C)C)C(C)C.[CH3:18][C:19]1([CH3:44])[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[C:25]2[CH:24]=[C:23]([C:31]3[N:36]=[C:35]([N:37]4[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]4)[CH:34]=[CH:33][CH:32]=3)[CH:22]=[CH:21][C:20]1=2.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1.CN(C=O)C>[CH3:18][C:19]1([CH3:44])[CH2:28][CH2:27][C:26]([CH3:29])([CH3:30])[C:25]2[CH:24]=[C:23]([C:31]3[N:36]=[C:35]([N:37]4[CH2:42][CH2:41][CH:40]([NH:1][C@@H:2]5[CH2:6][CH2:5][C@@H:4]([OH:7])[C@H:3]5[OH:8])[CH2:39][CH2:38]4)[CH:34]=[CH:33][CH:32]=3)[CH:22]=[CH:21][C:20]1=2
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참가 물질

9

반응물 6

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 13497976(1R,2S,3R)-3-aminocyclopentane-1,2-diolHCID 672484016'-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2,3,5,6-tetrahydro-1,2'-bipyridinyl-4-one

생성물 1

HCID 68380456(1R,2S,3R)-3-[6'-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-3,4,5,6-tetrahydro-2H-1,2'-bipyridinyl-4-ylamino]cyclopentane-1,2-diol

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

31 mg (0.199 mmol) of (1R,2S,3R)-3-aminocyclopentane-1,2-diol are dissolved in 3.5 ml of THF and 2 ml of DMF, and 33.8 μl of DIPEA are added. 80 mg (0.199 mmol) of 6′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2,3,5,6-tetrahydro-1,2′-bipyridinyl-4-one are added. The mixture is stirred at room temperature for 30 min, 23 μl (0.398 mmol) of glacial acetic acid are added, and the mixture is stirred for a further 10 min. 89 mg (0.398 mmol) of sodium triacetoxyborohydride are subsequently added. The reaction mixture is stirred at room temperature overnight, a concentrated sodium hydrogencarbonate solution is added, and the mixture is extracted twice with EA. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue is purified by means of preparative HPLC. The product is in the form of the hydrochloride.

후처리

  1. stirringthe mixture is stirred for a further 10 min
  2. stirringThe reaction mixture is stirred at room temperature overnight
  3. extractionthe mixture is extracted twice with EA
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by means of preparative HPLC

출처 및 근거

ORD 기록
ord-c23db8b055744c7585ec7a32f5ebaec0
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062015B2

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