Trifluoroacetic acid → HCID 131720917, compound

HRID 355519Notes

Reaction equation

HRID 355519 reaction equation
C(O)(C(F)(F)F)=O.[NH:8](C(OC(C)(C)C)=O)[C@H:9]([C:25]([C:27]([O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])=[O:28])=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1>C(Cl)Cl>[NH2:8][C@H:9]([C:25]([C:27]([O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:35])[CH3:34])=[O:28])=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131720918HCID 131720918, compound

Product 1

HCID 131720917HCID 131720917, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Eighty percent TFA in CH2Cl2 (20 mL, v/v) was added to an ice-cooled solution of Boc-Tyr(OBn)-CO2CH2CH2TMS (14.8 g, 31.4 mmol) in CH2Cl2 (40 mL). The resulting mixture was stirred for 1.0 minute before concentrating in vacuo. The procedure was repeated once more, and the resulting residue was diluted with CH2 Cl2 and saturated aqueous NaHCO3. The resulting mixture was filtered through celite. The organic layer was then separated, washed with saturated aqueous NaCl, and dried (MgSO4). Filtration and concentration in vacuo provided an oil which was further purified by flash chromatography (SiO2, CHCl3 :MeOH eluent) to give the desired product;

Workup

  1. concentrationbefore concentrating in vacuo
  2. additionthe resulting residue was diluted with CH2 Cl2 and saturated aqueous NaHCO3
  3. filtrationThe resulting mixture was filtered through celite
  4. customThe organic layer was then separated
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and concentration in vacuo
  8. customprovided an oil which
  9. customwas further purified by flash chromatography (SiO2, CHCl3 :MeOH eluent)

Sources & evidence

ORD record
ord-3f4944625dd240268898e5ca7f4dbec3
Source dataset
uspto-grants-1998_11
Patent number
US05830868

Reaction notes

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