Trifluoroacetic acid → HCID 59886940, compound

HRID 1279001Notes

Reaction equation

HRID 1279001 reaction equation
C(OC([NH:8][N:9]([C:11]([C@@H:13]1[CH2:17][C@@H:16]([S:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:15][N:14]1[S:28]([C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)(=[O:30])=[O:29])=[O:12])[CH3:10])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:10][N:9]([C:11]([C@@H:13]1[CH2:17][C@@H:16]([S:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH2:15][N:14]1[S:28]([C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)(=[O:29])=[O:30])=[O:12])[NH2:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59886944HCID 59886944, compound

Product 1

HCID 59886940HCID 59886940, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Step 22) 2 g (3.4 mmol) (2S,4R)-N′-[4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-N′-methyl-hydrazinecarboxylic acid tert-butyl ester in 9 ml CH2Cl2 were treated with 3.4 ml TFA for 2 h. The solution was concentrated, redissolved in toluene and evaporated. The residue was dissolved in ethyl acetate and sat. aq. NaHCO3, the layers were separated and the inorganic one was extracted with ethyl acetate, the combined organic ones were washed wit brine, dried over Na2SO4 and concentrated yielding 1.67 g (quant) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid N-methyl-hydrazide as white solid, MS: 486 (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionredissolved in toluene
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. customsat. aq. NaHCO3, the layers were separated
  6. extractionthe inorganic one was extracted with ethyl acetate
  7. washthe combined organic ones were washed wit brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-496d196a0fc74694afec2805847c0fd5
Source dataset
uspto-grants-2002_09
Patent number
US06444829B1

Reaction notes

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