Trifluoroacetic acid → HCID 137328749, compound

HRID 1432957Notes

Reaction equation

HRID 1432957 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[CH:17]=[C:16]1[CH2:24][N:25]1[C:30](=[O:31])[CH2:29][N:28]([S:32]([CH:35]=[CH:36][C:37]2[S:38][C:39]([Cl:42])=[CH:40][CH:41]=2)(=[O:34])=[O:33])[CH2:27][C@@H:26]1[C:43]([CH3:51])([CH3:50])[O:44][SiH2:45][C:46]([CH3:49])([CH3:48])[CH3:47])=O)(C)(C)C>C(Cl)Cl>[C:46]([SiH2:45][O:44][C:43]([CH3:51])([CH3:50])[C@@H:26]1[N:25]([CH2:24][C:16]2[NH:15][C:23]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[CH:17]=2)[C:30](=[O:31])[CH2:29][N:28]([S:32]([CH:35]=[CH:36][C:37]2[S:38][C:39]([Cl:42])=[CH:40][CH:41]=2)(=[O:33])=[O:34])[CH2:27]1)([CH3:49])([CH3:47])[CH3:48]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 137328750HCID 137328750, compound

Product 1

HCID 137328749HCID 137328749, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.25 mL) is added to a solution of 2-{2-(R)-(tert-butyl-dimethyl-silanyloxymethyl)-4-[2-(5-chloro-thiophen-2-yl)-ethenesulfonyl]-6-oxo-piperazin-1-ylmethyl}-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.025 g, 0.037 mmol) in CH2Cl2(0.5 mL) at room temperature. The reaction mixture is stirred for 2 h then concentrated to dryness. The residue is diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude product (0.019 g, 0.033 mmol) is used in the subsequent step without further purification.

Workup

  1. concentrationthen concentrated to dryness
  2. additionThe residue is diluted with CH2Cl2
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-385f4b7f8be7452ca34701b4cdf2e2a7
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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