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Lithium Hydroxide → HCID 10119718, 화합물

HRID 2085665
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HRID 2085665 반응식
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].[CH:23]1([NH:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][C:31]=2[N+:40]([O-:42])=[O:41])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.CCN=C=NCCCN(C)C>C1COCC1.CN(C1C=CN=CC=1)C.O1CCOCC1.C(OCC)(=O)C>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([NH:39][S:36]([C:33]3[CH:34]=[CH:35][C:30]([NH:29][CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[C:31]([N+:40]([O-:42])=[O:41])[CH:32]=3)(=[O:38])=[O:37])=[O:17])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1)([CH3:3])([CH3:4])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 3939Lithium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22660807HCID 22660807, 화합물HCID 22730084HCID 22730084, 화합물

생성물 1

HCID 10119718HCID 10119718, 화합물

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine
촉매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

실험 절차

A mixture of Example 5C (55 mg, 0.20 mmol) and 1M LiOH (0.3 mL) in THF (2 mL) was heated to 50° C., stirred for 3 hours, concentrated, dissolved in DMF (0.5 mL), and treated with a mixture of Example 3A (60 mg, 0.20 mmol), EDCI (96 mg, 0.50 mmol), and DMAP (10 mg) in dioxane (2.0 mL). The mixture was stirred for 16 hours, diluted with ethyl acetate (50 mL), washed sequentially with 1M HCl (5 mL), water (5 mL), and brine (5 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel, with 50% ethyl acetate/hexanes to provide a ˜2:1 mixture of diastereomers. MS (ESI(−)) m/e 540 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ8.63 (2d, 1H total), 8.33 (2d, 1H total), 7.95 (m, 1H), 7.82 and 7.78 (2d, 2H total), 7.45 (m, 1H), 7.30 (m, 2H), 3.71 (m, 1H), 2.28-0.95 (m, 20H), 0.86 and 0.75 (2s, 9H total).

후처리

  1. concentrationconcentrated
  2. dissolutiondissolved in DMF (0.5 mL)
  3. stirringThe mixture was stirred for 16 hours
  4. washwashed sequentially with 1M HCl (5 mL), water (5 mL), and brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel, with 50% ethyl acetate/hexanes
  9. customto provide
  10. additiona ˜2:1 mixture of diastereomers

출처 및 근거

ORD 기록
ord-f62fefd0a6c04aab9c2b0550472d9577
출처 데이터셋
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06720338B2

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