Dimethylformamide → HCID 58513752, compound

HRID 2362725Notes

Reaction equation

HRID 2362725 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)([O:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23]N(C)C=O.C(Cl)(=O)C(Cl)=O>ClCCl>[CH3:23][O:16][C:15](=[O:17])[CH2:14][O:13][C:10]1([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 58513728HCID 58513728, compound

Product 1

HCID 58513752HCID 58513752, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 2-(1-(tert-butoxycarbonyl)-3-(thiazol-2-yl)pyrrolidin-3-yloxy)acetic acid (7.5 g, 22.84 mmol) in dichloromethane (150 mL) was added N,N-dimethylformamide (1 mL) followed by dropwise addition of oxalyl chloride (1.999 mL, 22.84 mmol). The cold bath was then removed, and the reaction was stirred for 4 hours. Methanol (30 mL) was added to the ambient reaction, and the reaction was stirred for an additional 0.5 hours. The reaction was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 50% ethyl acetate in hexane, to give the product. MS ESI(+) m/z 342.8 [M+H]+.

Workup

  1. customThe cold bath was then removed
  2. additionMethanol (30 mL) was added to the ambient reaction
  3. stirringthe reaction was stirred for an additional 0.5 hours
  4. concentrationThe reaction was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with a gradient of 0 to 50% ethyl acetate in hexane
  7. customto give the product

Sources & evidence

ORD record
ord-5984bf63fefc4976995845801414e153
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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