Trifluoroacetic acid → HCID 19076546, compound

HRID 234540Notes

Reaction equation

HRID 234540 reaction equation
C([O:5]C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17]2([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[Cl:53])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[N:19]([S:27]([C:30]3[CH:31]=[C:32]4[C:36](=[CH:37][CH:38]=3)[N:35]([C:39]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[O:40])[CH2:34][CH2:33]4)(=[O:29])=[O:28])[C:18]2=[O:46])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:54]([OH:60])([C:56]([F:59])([F:58])[F:57])=[O:55]>C(Cl)Cl>[OH2:5].[F:57][C:56]([F:59])([F:58])[C:54]([OH:60])=[O:55].[Cl:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]([S:27]([C:30]1[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=1)[N:35]([C:39]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[O:40])[CH2:34][CH2:33]3)(=[O:29])=[O:28])[C:18](=[O:46])[C:17]2([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[Cl:53])[NH:16][CH2:15][CH2:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23358023HCID 23358023, compound

Product 1

HCID 19076546HCID 19076546, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.17 g of the compound obtained in EXAMPLE 222 in 7.5 ml of DCM is cooled to +4° C., 15 ml of TFA are added and the reaction mixture is stirred for 3 hours 15 minutes at +4° C. It is concentrated under vacuum, the residue is taken up with DCM and the solvent is evaporated off under vacuum, this operation being repeated twice. The residue is taken up with AcOEt, the organic phase is washed with water and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 0.6 g of the expected product after trituration in iso ether and then crystallization from a DCM/iso ether mixture. M.p.=133° C.

Workup

  1. concentrationIt is concentrated under vacuum
  2. customthe solvent is evaporated off under vacuum
  3. washthe organic phase is washed with water and with a saturated solution of NaCl
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-2615694e69924d609835e12391591627
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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