Trifluoroacetic anhydride → HCID 57855271, compound

HRID 2234814Notes

Reaction equation

HRID 2234814 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:25]3[N:8]([N:9]([CH3:26])[CH2:10][O:11][C:12]=3[C:13]=1[N:14]1[CH2:18][CH2:17][C@@H:16]([NH:19][C:20]3[S:21][CH:22]=[CH:23][N:24]=3)[CH2:15]1)[CH:7]=[C:6]([C:27]([OH:29])=[O:28])[C:5]2=[O:30].F[C:32](F)(F)[C:33](OC(=O)C(F)(F)F)=[O:34]>>[C:33]([N:19]([C:20]1[S:21][CH:22]=[CH:23][N:24]=1)[C@@H:16]1[CH2:17][CH2:18][N:14]([C:13]2[C:12]3=[C:25]4[C:4]([C:5](=[O:30])[C:6]([C:27]([OH:29])=[O:28])=[CH:7][N:8]4[N:9]([CH3:26])[CH2:10][O:11]3)=[CH:3][C:2]=2[F:1])[CH2:15]1)(=[O:34])[CH3:32]

Participants

3

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 44204638HCID 44204638, compound

Product 1

HCID 57855271HCID 57855271, compound

Procedure

A solution of product 36b (200 mg, 0.46 mmol, 1.0 eq.) in trifluoroacetic anhydride (5 mL) is heated to 90° C. for 6 hours. The reaction medium is cooled down to room temperature, the mixture is filtered and the filtrate is concentrated under reduced pressure. The obtained residue is re-crystallized from methanol and then purified by preparative HPLC (acetonitrile/H2O gradient). The expected product is obtained as a beige solid (25 mg, 88%).

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe obtained residue is re-crystallized from methanol
  4. custompurified by preparative HPLC (acetonitrile/H2O gradient)

Sources & evidence

ORD record
ord-5f7d209e134b48d2af91f3a046aec524
Source dataset
uspto-grants-2010_05
Patent number
US07713965B2

Reaction notes

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