(1-Ethoxycyclopropoxy)trimethylsilane → HCID 67126828, compound

HRID 1848918Notes

Reaction equation

HRID 1848918 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-61f0dbed7ad34d68b58d27ab93f44137
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

Loading…