(1-Ethoxycyclopropoxy)trimethylsilane → HCID 72748463, compound

HRID 1269021Notes

Reaction equation

HRID 1269021 reaction equation
[CH3:1][CH:2]([CH3:28])[CH:3]([NH:15][C:16]([CH:18]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20][NH:19]1)=[O:17])[CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1.C(O[C:32]1(O[Si](C)(C)C)[CH2:34][CH2:33]1)C.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:1][CH:2]([CH3:28])[CH:3]([NH:15][C:16]([CH:18]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20][N:19]1[CH:32]1[CH2:34][CH2:33]1)=[O:17])[CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1

Participants

6

Reactant 3

HCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 72762834HCID 72762834, compound

Product 1

HCID 72748463HCID 72748463, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

5-propyl-azepane-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide prepared by the methods described in examples 47, 48 (68 mg, 0.16 mmol) in MeOH (2 mL), acetic acid (0.1 mL) was added, followed by 1-[(ethyoxycyclopropyl)oxy]trimethylsilane (0.2 mL, 0.96 mmol), sodium cyanoborohydride (41 mg, 0.64 mmol), and 3 Å molecular sieves, heated to reflux for 3 hrs. Molecular sieves were filtered out and the reaction solvent was removed to obtain the crude material. Purification was carried by silica gel column chromatography (10% MeOH/DCM) and HPLC to provide the title compound (44 mg, 59%). 1H NMR (300 MHz, CD3OD) δ 5.20 (d, J=5.4, 1), 4.15 (d, J=6.6, 1), 4.08 (dd, J=5.4, 9.9, 1), 3.96 (d, J=3.0, 1), 3.88 (t, J=13.2, 1), 3.62 (m, 1), 3.56 (dd, J=3.3, 10.2, 1), 3.14 (m, 1), 2.82 (m, 1), 2.13 (m, 2), 2.05 (s, 3), 1.99–1.30 (m, 10), 0.96 (m, 9), 0.51 (m, 4); MS(ESPOS): 459 [M+H]+.

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureto reflux for 3 hrs
  4. filtrationMolecular sieves were filtered out
  5. customthe reaction solvent was removed
  6. customto obtain the crude material
  7. customPurification

Sources & evidence

ORD record
ord-e1888c9c107b4990b5e94408365d2bb0
Source dataset
uspto-grants-2007_04
Patent number
US07199106B2

Reaction notes

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