Dimethylformamide → HCID 67222560, compound

HRID 876580Notes

Reaction equation

HRID 876580 reaction equation
[C:1]([O:5][C:6](=[O:20])[C@H:7]([O:16][C:17](=[O:19])[CH3:18])[C@@H:8]([O:12][C:13](=[O:15])[CH3:14])[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[Cl:32][CH2:33][CH2:34][NH:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=1>C(Cl)Cl.N1C=CC=CC=1>[C:17]([O:16][C@H:7]([C@@H:8]([O:12][C:13](=[O:15])[CH3:14])[C:9]([N:35]([CH2:34][CH2:33][Cl:32])[C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:44])([F:45])[F:43])=[CH:38][CH:37]=1)=[O:11])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:20])(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 141434761-(1,1-Dimethylethyl) (2R,3R)-2,3-bis(acetyloxy)butanedioateHCID 65029835HCID 65029835, compound

Product 1

HCID 67222560HCID 67222560, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (R,R)-2,3-bis(acetyloxy)-butanedioic acid mono tert-butyl ester (3.25 g: Tetrahedron, 45, 3071-3080, 1989) in CH2Cl2 (65 mL), were added oxalyl chloride (1.06 mL) and DMF (50 microL) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes then pyridine (3.82 mL) was added into the mixture at the same temperature. The reaction mixture was stirred at the same temperature for 5 minutes. To the mixture, was added a solution of compound 54-2 (2.5 g) in CH2Cl2 (12.5 mL) at 0° C. The mixture was stirred for 1 hour at the same temperature. Then the mixture was concentrated in vacuo and the resulting residue was suspended in water. The mixture was extracted with EtOAc and the organic layer was washed with 1N HCl aq., sat. NaHCO3 aq., brine, and it was dried with anhyd. Na2SO4. The solvent was removed under reduced pressure to obtain compound 54-3 (5.7 g) as brown oil.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 5 minutes
  2. stirringThe mixture was stirred for 1 hour at the same temperature
  3. concentrationThen the mixture was concentrated in vacuo
  4. extractionThe mixture was extracted with EtOAc
  5. washthe organic layer was washed with 1N HCl aq., sat. NaHCO3 aq., brine, and it
  6. customwas dried with anhyd
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b2e63aaab69c415a93f2fd1ba5763133
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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