Ethylene Oxide → HCID 85082150, compound

HRID 1269092Notes

Reaction equation

HRID 1269092 reaction equation
CCN(C(C)C)C(C)C.[CH2:10]1[O:12][CH2:11]1.[CH3:13][CH:14]([CH3:40])[CH:15]([NH:27][C:28]([CH:30]1[CH2:34][CH:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][NH:31]1)=[O:29])[CH:16]1[CH:21]([OH:22])[CH:20]([OH:23])[CH:19]([OH:24])[CH:18]([S:25][CH3:26])[O:17]1>CO>[CH3:13][CH:14]([CH3:40])[CH:15]([NH:27][C:28]([CH:30]1[CH2:34][CH:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][N:31]1[CH2:10][CH2:11][OH:12])=[O:29])[CH:16]1[CH:21]([OH:22])[CH:20]([OH:23])[CH:19]([OH:24])[CH:18]([S:25][CH3:26])[O:17]1

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 81531DiisopropylethylamineHCID 780406994-Pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

Product 1

HCID 85082150HCID 85082150, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-4 °C

Procedure

DIEA (0.1 mL, 0.57 mmol) and liquid ethylene oxide (3 mL) were added to a stirred solution of crude 4-pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide, prepared as in Example 10 (237.4 mg), in anhydrous methanol (10 mL), at 0° C. and under nitrogen. The resulting solution was stirred at −4° C. for 18 h and evaporated to dryness. The residue obtained was purified by chromatography over silica gel with an eluent of 5% methanolic ammonia in dichloromethane. The desired fractions were evaporated and the residue lyophilized (deuterium oxide/anhydrous acetonitrile, 1:1, v/v, 10 mL) to furnish the title compound as a fluffy white powder (50.1 mg, 30.2%); TLC, Rf=0.68 (14% methanolic ammonia in dichloromethane); 1H NMR (300 MHz) δ 5.40 (d, J=5.8, 1), 4.55 (m, 1), 4.24 (s, 1), 4.17–4.11 (m, 1), 3.99–3.89 (m, 4), 3.69–3.65 (m, 1), 3.47 (d, J=4.4, 2), 3.01 (m, 1), 2.33 (br s, 4), 2.18 (s, 4), 1.57–1.32 (m, 9), 0.94–0.87 (m, 9).

Workup

  1. customevaporated to dryness
  2. customThe residue obtained
  3. customwas purified by chromatography over silica gel with an eluent of 5% methanolic ammonia in dichloromethane
  4. customThe desired fractions were evaporated

Sources & evidence

ORD record
ord-2a561812efdf48a6b6daa66e83113e08
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

Loading…