Triethylsilane → HCID 86585073, compound

HRID 1264422Notes

Reaction equation

HRID 1264422 reaction equation
[CH2:1]([N:8]([CH3:41])[C:9](=[O:40])[CH2:10][CH2:11][C@@H:12]1[CH2:16][C@@H:15]([S:17]CC2C=CC(OC)=CC=2)[CH2:14][N:13]1[S:27]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)(=[O:29])=[O:28])[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]([CH3:41])[C:9](=[O:40])[CH2:10][CH2:11][C@@H:12]1[CH2:16][C@@H:15]([SH:17])[CH2:14][N:13]1[S:27]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)(=[O:29])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 70000374HCID 70000374, compound

Product 1

HCID 86585073HCID 86585073, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

To 131 mg (0.23 mmol) (2R,4R)-N-Benzyl-3-[4-(4-methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-N-methyl-propionamide in 8 ml TFA were added 0.37 ml (2.3 mmol, 10 eq) triethyl silane at 0° C. and the solution was stirred for 60 min at 80° C., evaporated, twice suspended in toluene and evaporated. The crude product was purified with prep. HPLC using a RPC18 column yielding 17 mg (2R,4R)-N-Benzyl-3-[4-mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-N-methyl-propionamide as light yellow gum, MS: 469 (MH+).

Workup

  1. customevaporated
  2. customevaporated
  3. customThe crude product was purified with prep

Sources & evidence

ORD record
ord-84c6b697847d4e46b5c8083f773a9dd6
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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