Oxalyl chloride → HCID 59715779, compound

HRID 2043536Notes

Reaction equation

HRID 2043536 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:16][C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:23])=O>CN(C=O)C.ClCCl>[Cl:23][C:17](=[O:19])[CH2:16][C@@H:12]1[CH2:13][CH2:14][CH2:15][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 10869111(S)-1-Cbz-2-pyrrolidineacetic acid

Product 1

HCID 59715779HCID 59715779, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To an argon purged round bottom flask fitted with a magnetic stirbar was added (S)-2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)acetic acid (235 mg, 0.893 mmol) followed by anhydrous dichloromethane (5 mL). The reaction was treated with anhydrous DMF (2 drops ˜5 μL). The flow of argon was stopped, and the reaction vessel fitted with a balloon. Oxalyl chloride (0.12 mL, 1.38 mmol) was added in two portions, resulting in effervescence. The reaction was stirred at room temperature for 3 hours, before being concentrated to dryness under reduced pressure and dried overnight under high vacuum.

Workup

  1. customTo an argon purged round bottom flask fitted with a magnetic stirbar
  2. customthe reaction vessel fitted with a balloon
  3. customresulting in effervescence
  4. concentrationbefore being concentrated to dryness under reduced pressure
  5. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-0a5024b4570e478d92509449fe26d33b
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

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