HCID 69543759, compound → HCID 86584807, compound

HRID 1278997Notes

Reaction equation

HRID 1278997 reaction equation
COC1C=CC(C[S:8][C@H:9]2[CH2:13][N:12]([S:14]([C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=3)(=[O:16])=[O:15])[C@H:11]([C:27]([NH:29][NH2:30])=[O:28])[CH2:10]2)=CC=1>C(O)(C(F)(F)F)=O.C([SiH](C(C)C)C(C)C)(C)C>[SH:8][C@H:9]1[CH2:13][N:12]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)(=[O:15])=[O:16])[C@H:11]([C:27]([NH:29][NH2:30])=[O:28])[CH2:10]1

Participants

4

Reactant 1

HCID 69543759HCID 69543759, compound

Product 1

HCID 86584807HCID 86584807, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 138754Silane, tris(1-methylethyl)-Solvent

Procedure

(step 9) 150 mg (0.3 mmol, 1.0 eq) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid hydrazide in 5 ml TFA and 0.65 ml triisopropylsilane were stirred for 3 d at RT. The solvent was evaporated and the residue redissolved in sat. NaHCO3 solution:ethyl acetate, the phases were separated and the inorganic one was extracted with ethyl acetate. The combined organic phases were washed with water and brine. Column chromatography yields 68 mg ( 61%) (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid hydrazide as white foam, MS: 352 (MH+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue redissolved in sat. NaHCO3 solution
  3. customethyl acetate, the phases were separated
  4. extractionthe inorganic one was extracted with ethyl acetate
  5. washThe combined organic phases were washed with water and brine

Sources & evidence

ORD record
ord-24816c04d3b1441fbe3e146c337993d5
Source dataset
uspto-grants-2002_09
Patent number
US06444829B1

Reaction notes

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