Trifluoroacetic acid → Trifluoroacetic acid

HRID 1278995Notes

Reaction equation

HRID 1278995 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23]([NH:25][N:26]([CH3:37])[S:27]([C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)(=[O:29])=[O:28])=[O:24])=O)(C)(C)C.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl>[CH3:37][N:26]([S:27]([C:30]1[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=1)(=[O:29])=[O:28])[NH:25][C:23]([C@@H:9]1[CH2:10][C@@H:11]([S:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:12][NH:8]1)=[O:24].[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69543822HCID 69543822, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 69543844HCID 69543844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(step 5) 2.37 g (4.3 mmol) (2S,4R)-2-[N′-Methyl-N′-(4-methyl-phenylsulfonyl)-hydrazinocarbonyl]-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid 1-tert-butyl ester in 10 ml CH2Cl2 were treated with 4 ml TFA at 0° C. and kept in the freezer over night. The solvent was evaporated, the crude material was dissolved and evaporated with toluene (2×) and hexane (3×) yielding (2S,4R)-2-[N′-Methyl-N′-(4-methyl-phenylsulfonyl)-hydrazinocarbonyl]-4-(4-methoxy-benzylsulfanyl)-pyrrolidine as TFA salt as crude product, which was subjected to the following reaction without further purification.

Workup

  1. waitkept in the freezer over night
  2. customThe solvent was evaporated
  3. dissolutionthe crude material was dissolved
  4. customevaporated with toluene (2×) and hexane (3×)

Sources & evidence

ORD record
ord-3091c1ba253d40c1bbc2b6be3f172af7
Source dataset
uspto-grants-2002_09
Patent number
US06444829B1

Reaction notes

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