Trifluoroacetic acid → HCID 58181678, compound

HRID 876590Notes

Reaction equation

HRID 876590 reaction equation
[C:1]([O:4][C@H:5]([C@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[CH2:24][N:23]([CH3:28])[C:22]3=[O:29])[C:14]1=[O:30])[C:6]([O:8]C(C)(C)C)=[O:7])(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:4][C@H:5]([C@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[CH2:24][N:23]([CH3:28])[C:22]3=[O:29])[C:14]1=[O:30])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 58181624HCID 58181624, compound

Product 1

HCID 58181678HCID 58181678, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 70-3 (85 mg) in CH2Cl2 (2.5 mL) at 0° C. was added TFA (0.5 mL) dropwise. The mixture was stirred for 1 h at 0° C. and at rt for 30 min whereupon an additional portion of TFA (0.5 mL) was added. After an additional 1 h at rt, the mixture was diluted with CH2Cl2 and concentrated to dryness under reduced pressure. The crude mixture was redissolved in CH2Cl2 and concentrated and this protocol was repeated 5 times with to afford compound 70-4 (65 mg) as a light semisolid. LC-MS: M+H=363. This material was used without further purification.

Workup

  1. additionwas added
  2. concentrationconcentrated to dryness under reduced pressure
  3. dissolutionThe crude mixture was redissolved in CH2Cl2
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-09d8ed7c11b440cf8432ac28f9515adb
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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