Trifluoroacetic acid → HCID 10421193, compound

HRID 346178Notes

Reaction equation

HRID 346178 reaction equation
C(OC([NH:8][C:9](=[O:22])[C@H:10]([CH2:12][S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[NH2:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][S:13][CH2:12][C@@H:10]([C:9]([NH2:8])=[O:22])[NH2:11])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86742687HCID 86742687, compound

Product 1

HCID 10421193HCID 10421193, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat the product of Step 1 (2.79 g) in CH2Cl2 (40 ml) with trifluoroacetic acid (10 ml) at room temperature for 18 hr. Concentrate the reaction mixture in vacuo. Dissolve the residue in CH2Cl2 and concentrate in vacuo (twice). Dissolve the white solid in EtOAc and extract with 10% sodium bicarbonate solution. Dry (MgSO4) the EtOAc and concentrate in vacuo to give the title compound, a white solid (1.53 g) m.p. 94°-95°, [α]D26 =-1.3° (MeOH).

Workup

  1. concentrationConcentrate the reaction mixture in vacuo
  2. dissolutionDissolve the residue in CH2Cl2
  3. concentrationconcentrate in vacuo (twice)
  4. dissolutionDissolve the white solid in EtOAc
  5. extractionextract with 10% sodium bicarbonate solution
  6. dry with materialDry (MgSO4) the EtOAc
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-865d7b4b23a44a719ffa8a45f3c39514
Source dataset
uspto-grants-1991_10
Patent number
US05061710

Reaction notes

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