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Dichloromethane → HCID 86717250, 화합물

HRID 595381
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HRID 595381 반응식
C([O:4][C@@H:5]1[C@@H:10]([N:11]=[N+:12]=[N-:13])[C@@H:9]([O:14]C(=O)C)[C@@H:8]([CH2:18][O:19]C(=O)C)[O:7][C@H:6]1[S:23][C@@H:24]1[O:37][C@H:36]([CH2:38][O:39]C(=O)C)[C@H:31]([O:32]C(=O)C)[C@H:30]([N:43]=[N+:44]=[N-:45])[C@H:25]1[O:26]C(=O)C)(=O)C.C(Cl)Cl.C[O-].[Na+].CCCCCCC.CCOC(C)=O>CO>[N:11]([C@H:10]1[C@@H:9]([OH:14])[C@@H:8]([CH2:18][OH:19])[O:7][C@@H:6]([S:23][C@@H:24]2[O:37][C@H:36]([CH2:38][OH:39])[C@H:31]([OH:32])[C@H:30]([N:43]=[N+:44]=[N-:45])[C@H:25]2[OH:26])[C@@H:5]1[OH:4])=[N+:12]=[N-:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 10942334Sodium MethoxideHCID 21899848Ethylacetate heptaneHCID 44514727HCID 44514727, 화합물

생성물 1

HCID 86717250HCID 86717250, 화합물수율 75.6%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

Compound 10 (160 mg, 0.00024 mol) was dissolved in dry MeOH (2.6 mL) and dry CH2Cl2 (1.6 mL), and NaOMe (1M, 24 μL, 24 μmol) was added. The reaction was monitored by TLC (heptane:EtOAc 1:1 and D:M 5:1). When the reaction was complete, the mixture was neutralized with Duolite C436 until pH 7, filtered and washed with MeOH. The filtered solution was concentrated under reduced pressure. The residue was purified by flash chromatography (Eluent: CH2Cl2:MeOH, 5:1) to give pure 11 (74.1 mg, 75%). 1H NMR in CDCl3 δ 4.72 (d, 2H, J=9.7 Hz, H-1, H-1′), 3.95 (br s, 2H, H-4, H-4′), 3.84 (t, 2H, J=9.8 Hz, H-2, H-2′), 3.74 (dd, 2H, J=11.47 Hz, 7.23 Hz, H-6, H-6′), 3.64 (dd, 2H, J=11.48 Hz, 4.72 Hz, H-6, H6′), 3.60-3.55 (ddd, 2H, 7.15 Hz, 4.67 Hz, 0.93 Hz, H-5, H-5′), 3.36 (dd, 2H, J=10 Hz, 3.05 Hz, H-3, H-3′).

후처리

  1. filtrationfiltered
  2. washwashed with MeOH
  3. concentrationThe filtered solution was concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (Eluent: CH2Cl2:MeOH, 5:1)

출처 및 근거

ORD 기록
ord-60b533b6aad040df8ba3518835469075
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09243021B2

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