Dichloromethane → HCID 86717250, compound

HRID 595381Notes

Reaction equation

HRID 595381 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 86717250HCID 86717250, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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′).

Workup

  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)

Sources & evidence

ORD record
ord-60b533b6aad040df8ba3518835469075
Source dataset
uspto-grants-2016_01
Patent number
US09243021B2

Reaction notes

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