Triethylsilane → (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid N'-isobutyl hydrazide

HRID 1278993Notes

Reaction equation

HRID 1278993 reaction equation
[CH2:1]([NH:5][NH:6][C:7]([C@@H:9]1[CH2:13][C@@H:12]([S:14]CC2C=CC(OC)=CC=2)[CH2:11][N:10]1[S:24]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)(=[O:26])=[O:25])=[O:8])[CH:2]([CH3:4])[CH3:3].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([NH:5][NH:6][C:7]([C@@H:9]1[CH2:13][C@@H:12]([SH:14])[CH2:11][N:10]1[S:24]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)(=[O:26])=[O:25])=[O:8])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69543784(2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid N'-isobutyl-hydrazide

Product 1

HCID 86584806(2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid N'-isobutyl hydrazideYield 86.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(step 2) 222 mg (0.42 mmol) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid N′-isobutyl-hydrazide in 10 ml TFA were treated with 0.68 ml (4.2 mmol, 10 eq) triethylsilane at 80° C. for 90 min. The solvent was evaporated in vacuo and the crude product was purified by flash chromatography yielding 148 mg (86%) (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid N′-isobutyl hydrazide as light yellow crystalline, MS: 408 (MH+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-73a161b84b734403af71ca2d0cf9765f
Source dataset
uspto-grants-2002_09
Patent number
US06444829B1

Reaction notes

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