(1-Ethoxycyclopropoxy)trimethylsilane → HCID 67126828, compound

HRID 624439Notes

Reaction equation

HRID 624439 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])[CH2:2]1.C(O[C:25]1(O[Si](C)(C)C)[CH2:27][CH2:26]1)C.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH:25]1([N:1]2[CH2:6][CH2:5][O:4][CH:3]([CH2:7][NH:8][C:9]3[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:16])=[O:17])=[CH:11][C:10]=3[N+:19]([O-:21])=[O:20])[CH2:2]2)[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 67126454HCID 67126454, compound

Product 1

HCID 67126828HCID 67126828, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of EXAMPLE 369B (0.633 g) and (1-ethoxycyclopropoxy)trimethylsilane (1.601 mL) in anhydrous methanol (15 mL) and acetic acid 1.717 mL) was refluxed for 30 minutes and allowed to cool to room temperature. Sodium cyanoborohydride (0.377 g) was then added and the mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated to dryness. The residue was mixed with 5% aqueous Na2CO3 solution (25 mL) and extracted with ethyl acetate. The crude product was purified on a silica gel column eluting with 5% to 10% methanol in dichloromethane to provide the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additionThe residue was mixed with 5% aqueous Na2CO3 solution (25 mL)
  3. extractionextracted with ethyl acetate
  4. customThe crude product was purified on a silica gel column
  5. washeluting with 5% to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-37978d9f8aa64f2da19254a88591b48e
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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