Triethylsilane → HCID 86584808, compound

HRID 1279000Notes

Reaction equation

HRID 1279000 reaction equation
[CH2:1]([N:8]([S:50]([C:53]1[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][CH:54]=1)(=[O:52])=[O:51])[NH:9][C:10]([C@@H:12]1[CH2:16][C@@H:15]([S:17]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:14][N:13]1[S:37]([C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=1)(=[O:39])=[O:38])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([N:8]([S:50]([C:53]1[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][CH:54]=1)(=[O:52])=[O:51])[NH:9][C:10]([C@@H:12]1[CH2:16][C@@H:15]([SH:17])[CH2:14][N:13]1[S:37]([C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=1)(=[O:39])=[O:38])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69543905HCID 69543905, compound

Product 1

HCID 86584808HCID 86584808, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(step 13) To 148 mg (0.17 mmol) ) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid N′-benzyl-N′-(4-methoxy-benzenesulfonyl)-hydrazide in 3.0 ml TFA were added 276 μl (1.73 mmol, 10 eq) triethylsilane at 0° C. The mixture was stirred at RT for 30 min, the solvent was evaporated and the residue was redissolved in ethyl acetate, sat. aq. NaHCO3 solution, the layers were separated and the inorganic one extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography with a gradient of ethyl acetate:hexane (1:1.5 to 1:1) yielding 76 mg (72%) (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid N′-benzyl-N′-(4-methoxy-benzenesulfonyl)-hydrazide as white foam, MS: 612 (MH+).

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue was redissolved in ethyl acetate
  3. customsat. aq. NaHCO3 solution, the layers were separated
  4. extractionthe inorganic one extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by flash chromatography with a gradient of ethyl acetate:hexane (1:1.5 to 1:1)

Sources & evidence

ORD record
ord-7d79c0ab48f74f6ab821baa03c9fe451
Source dataset
uspto-grants-2002_09
Patent number
US06444829B1

Reaction notes

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