Lithium Chloride → HCID 57551962, compound

HRID 1366306Notes

Reaction equation

HRID 1366306 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14](OS(C)(=O)=O)[C@H:13]2[O:21][CH2:22][C:23]([O:26][CH3:27])([O:24][CH3:25])[C@@H:12]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-:28].[Li+]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([Cl:28])[C@H:13]2[O:21][CH2:22][C:23]([O:26][CH3:27])([O:24][CH3:25])[C@@H:12]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 57551982HCID 57551982, compound

Product 1

HCID 57551962HCID 57551962, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of compound 12e (550 mg, 1.37 mmol) in DMF (30 mL) was added lithium chloride (721 mg, 13.7 mmol). After stirring for 120 minutes at 120° C. the reaction was concentrated in vacuo. The residue was diluted with CH2Cl2 (50 mL) washed with water (1×20 mL), dried with MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (5-66% isohexane:EtOAc) to give the title compound (330 mg, 72%) as a yellow oil. MS M+H 342, 344.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was diluted with CH2Cl2 (50 mL)
  3. washwashed with water (1×20 mL)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (5-66% isohexane:EtOAc)

Sources & evidence

ORD record
ord-cd71827ccfb84c7d930faacf42a24eec
Source dataset
uspto-grants-2011_02
Patent number
US07893067B2

Reaction notes

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