Methanol → HCID 72758525, compound
Reaction equation
CCN(C(C)C)[CH:4]([CH3:6])[CH3:5].[CH3:10][CH:11]([CH3:37])[CH:12]([NH:24][C:25]([CH:27]1[CH2:31][CH:30]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][NH:28]1)=[O:26])[CH:13]1[CH:18]([OH:19])[CH:17]([OH:20])[CH:16]([OH:21])[CH:15]([S:22][CH3:23])[O:14]1.C[OH:39]>>[CH3:10][CH:11]([CH3:37])[CH:12]([NH:24][C:25]([CH:27]1[CH2:31][CH:30]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][N:28]1[CH2:5][CH:4]([OH:39])[CH3:6])=[O:26])[CH:13]1[CH:18]([OH:19])[CH:17]([OH:20])[CH:16]([OH:21])[CH:15]([S:22][CH3:23])[O:14]1Participants
Conditions
- Temperature
- -4 °C
Procedure
DIEA (0.1 mL, 0.58 mmol, 1 equiv) and R(+)-propylene oxide (3 mL) were added to a stirred cool solution of crude 4-pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide (307.6 mg, 0.58 mmol, 1 equiv), prepared as in Example 10, 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 6% methanolic ammonia in dichloromethane. The desired fractions were evaporated, and lyophilized (deuterium oxide/anhydrous acetonitrile, 1:1, v/v, 20 mL) to furnish the title compound as a fluffy white powder (91 mg, 48%).
Workup
- temperaturecool
- customat 0° C.
- customevaporated to dryness
- customThe residue obtained
- customwas purified by chromatography over silica gel, with an eluent of 6% methanolic ammonia in dichloromethane
- customThe desired fractions were evaporated
Sources & evidence
- ORD record
- ord-83a58056ef8647c381643d044156f762
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199105B2
Reaction notes
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