Triethylamine → HCID 58743802, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([O:28][CH2:29][CH2:30][OH:31])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:32])[CH2:10][CH2:9]1)[CH3:7].[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(N(CC)CC)C.[NH4+].[Cl-]>C1COCC1>[OH:32][C@@H:13]1[CH2:14][CH:15]2[C@:20]([CH3:21])([CH2:19][CH2:18][C@H:17]([O:28][CH2:29][CH2:30][O:31][S:35]([CH3:34])(=[O:37])=[O:36])[CH2:16]2)[C@@H:22]2[C@@H:12]1[C@H:11]1[C@:25]([CH3:26])([C@@H:24]([OH:27])[CH2:23]2)[C@@H:8]([C@H:6]([CH3:7])[CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:33])[CH2:9][CH2:10]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The compound of example 1B (1.0 g, 2.1 mmol) was dissolved in THF (21 mL) and cooled to 0° C. To the cooled solution was added methanesulfonyl chloride (0.25 mL, 3.21 mmol) followed by the dropwise addition of triethylamine (0.45 mL, 3.21 mmol). The reaction solution was warmed to room temperature and allowed to stir overnight. Saturated aqueous NH4Cl was added and the solution was extracted twice with ethyl acetate. The organic phase was washed with brine, dried (MgSO4), concentrated and purified via column chromatography (1:1 hexanes:ethyl acetate). The yield of the product was 429 mg (37%).
Workup
- temperatureThe reaction solution was warmed to room temperature
- extractionthe solution was extracted twice with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- custompurified via column chromatography (1:1 hexanes:ethyl acetate)
Sources & evidence
- ORD record
- ord-7d3412d4d8e443e689d276db39e94694
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141559B2
Reaction notes
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