Trifluoroacetic acid → HCID 44271005, compound

HRID 1459067Notes

Reaction equation

HRID 1459067 reaction equation
[CH3:1][C:2]([CH3:44])([CH3:43])[C@H:3]([NH:8][C:9](=[O:42])[C@@H:10]([CH2:18][C@@H:19]([OH:41])[CH2:20][S:21]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4](=[O:7])[NH:5][CH3:6].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH3:43][C:2]([CH3:1])([CH3:44])[C@H:3]([NH:8][C:9](=[O:42])[C@@H:10]([CH2:18][C@@H:19]([OH:41])[CH2:20][SH:21])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4](=[O:7])[NH:5][CH3:6]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57197061HCID 57197061, compound

Product 1

HCID 44271005HCID 44271005, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.700 g (1.136 mmol) of the product of Example 33 and 0.363 mL (2.273 mmol) of triethylsilane dissolved in 10 mL of dichloromethane was dropwise added 10 mL of trifluoroacetic acid. The reaction mixture was stirred at room temperature for 0.5 h and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with EtOAc/Hexanes (gradient: 1:3-1:1) to provide 0.263 g (62%) of the desired product as a colorless oil. Electrospray Mass Spec: 375.4 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with EtOAc/Hexanes (gradient: 1:3-1:1)

Sources & evidence

ORD record
ord-b8fedff68f464e13857e4b5f5d1fb7d3
Source dataset
uspto-grants-1998_12
Patent number
US05852213

Reaction notes

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