Trifluoroacetic acid → HCID 10311006, compound

HRID 349507Notes

Reaction equation

HRID 349507 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C@@H:21]([CH3:38])[C:22]([N:24]([CH:35]([CH3:37])[CH3:36])[CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)=[O:23])[C:17]1=[O:39])(=[O:14])=[O:13])[CH:6]=[CH:5]2.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:27][CH2:26][CH2:25][N:24]([CH:35]([CH3:37])[CH3:36])[C:22](=[O:23])[C@@H:21]([N:18]1[CH2:19][CH2:20][C@H:16]([NH:15][S:12]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=3)[CH:8]=2)(=[O:13])=[O:14])[C:17]1=[O:39])[CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11284653HCID 11284653, compound

Product 1

HCID 10311006HCID 10311006, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-[[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl](isopropyl)amino]ethylcarbamate (0.21 g) was dissolved in DCM (4 ml), and trifluoroacetic acid (4 ml) was added. The mixture was stirred at room temperature for 2.5 h and then concentrated under reduced pressure. The residue was partitioned between saturated sodium bicarbonate solution and DCM, and the organic layer was separated, dried (over magnesium sulphate) and concentrated under reduced pressure. The residue was purified using SPE (silica, eluting with DCM, diethyl ether, ethyl acetate, methanol and methanol:10% aqueous ammonia) to give the title compound (0.124 g) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between saturated sodium bicarbonate solution and DCM
  3. customthe organic layer was separated
  4. dry with materialdried (over magnesium sulphate)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. washSPE (silica, eluting with DCM, diethyl ether, ethyl acetate, methanol and methanol:10% aqueous ammonia)

Sources & evidence

ORD record
ord-50e90fb2321c41138d86e6b64dc10154
Source dataset
uspto-grants-2007_02
Patent number
US07179835B2

Reaction notes

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