Dichloromethane → HCID 15946646, compound

HRID 558021Notes

Reaction equation

HRID 558021 reaction equation
[N:1]([C@H:4]1[C@@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:8]([O:18][CH2:19]C2C=CC=CC=2)[C@@H:7]([CH2:26][O:27]CC2C=CC=CC=2)[O:6][C@@H:5]1[CH2:35][P:36]([O:41][CH2:42][CH3:43])(=[O:40])[O:37][CH2:38][CH3:39])=[N+:2]=[N-:3].C(Cl)Cl>CC(O)=O.CC(OC(C)=O)=O.OS(O)(=O)=O.CC(OC(C)=O)=O>[C:5]([O:27][CH2:26][C@H:7]1[O:6][C@H:5]([CH2:35][P:36]([O:37][CH2:38][CH3:39])(=[O:40])[O:41][CH2:42][CH3:43])[C@@H:4]([N:1]=[N+:2]=[N-:3])[C@@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:8]1[O:18][CH2:19][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:6])[CH3:4]

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 15946645HCID 15946645, compound

Product 1

HCID 15946646HCID 15946646, compoundYield 169.2%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 7918Acetic AnhydrideSolventHCID 21895370AcOH AcOAcSolvent

Procedure

Compound 3 (3.2 g, 5.2 mmol) was dissolved in HOAc/Ac2O (1:1, 32 mL). Ten drops of 1% H2SO4 in Ac2O was added. After stirring overnight the mixture was poured into a separation funnel containing ice and CH2Cl2. The organic phase was separated, filtered through a plug of silica and concentrated. The residue was purified by column chromatography to give 4 (2.48 g, 4.4 mmol, 84%). 13C-NMR (CDCl3) 170.41, 137.41, 136.95, 128.34-127.75, 77.77, 77.60, 74.01, 73.39, 72.17, 71.89, 69.26, 62.47, 61.82, 61.73, 60.50, 60.37, 27.57 (d, J=141 Hz), 20.59, 16.27, 16.19; 31P-NMR (CDCl3) 27.50; [α]D+37 (c 1.0, CHCl3).

Workup

  1. additionwas poured into a separation funnel
  2. customThe organic phase was separated
  3. filtrationfiltered through a plug of silica
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6232f770218248f1b3fa96cd19a8c8fb
Source dataset
uspto-grants-2011_11
Patent number
US08062641B2

Reaction notes

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