Dimethylformamide → HCID 86669324, compound

HRID 2170263Notes

Reaction equation

HRID 2170263 reaction equation
[CH2:1]([O:8][C@H:9]([C:13]([CH3:33])([CH3:32])[CH2:14][O:15][S:16]([CH2:19][CH2:20][CH2:21][S:22]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:24])=[O:23])(=[O:18])=[O:17])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34](Cl)(=O)[C:35](Cl)=O.CN(C)C=O>ClCCl>[CH2:1]([O:8][C@H:9]([C:13]([CH3:33])([CH3:32])[CH2:14][O:15][S:16]([CH2:19][CH2:20][CH2:21][S:22]([O:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:23])=[O:24])(=[O:17])=[O:18])[C:10]([O:12][CH2:34][CH3:35])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86669325HCID 86669325, compound

Product 1

HCID 86669324HCID 86669324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred 0° C. solution of (2R)-2-benzyloxy-3,3-dimethyl-4-(3-phenoxysulfonylpropylsulfonyloxy)butanoic acid (Example 8(a), Step 3) (0.8 g) in dichloromethane (10 mL), was added oxalyl chloride (0.28 mL) followed by a drop of N,N-dimethylformamide. The reaction mixture was stirred for 1 hour and concentrated in vacuo. The resulting residue was dissolved in dichloromethane (10 mL), to which was added ethanol (2 mL). The reaction mixture was stirred overnight at room temperature. The volatiles were removed, and the residual material was purified by silica gel chromatography (hexanes/ethyl acetate 70:30) to afford ethyl (2R)-2-benzyloxy-3,3-dimethyl-4-(3-phenoxysulfonylpropylsulfonyloxy)butanoate (0.70 g).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in dichloromethane (10 mL), to which
  3. additionwas added ethanol (2 mL)
  4. stirringThe reaction mixture was stirred overnight at room temperature
  5. customThe volatiles were removed
  6. customthe residual material was purified by silica gel chromatography (hexanes/ethyl acetate 70:30)

Sources & evidence

ORD record
ord-6fa6b5a5bc4d4e0e96ce7406572e7db0
Source dataset
uspto-grants-2015_06
Patent number
US09051248B2

Reaction notes

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