Hydrochloric Acid → HCID 89590945, compound
Reaction equation
[CH2:1]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[OH:10])[CH2:2][CH:3]=[CH2:4].CCN(C(C)C)C(C)C.Cl[C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:32][C:33]([CH3:40])([CH3:39])[C@@H:34]([C:36]([OH:38])=[O:37])[NH2:35].[OH-].[Na+].Cl>O1CCOCC1>[CH2:1]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[O:10][C:21]([NH:35][C@H:34]([C:36]([OH:38])=[O:37])[C:33]([CH3:40])([CH3:39])[CH3:32])=[O:23])[CH2:2][CH:3]=[CH2:4]Participants
Conditions
- Temperature
- 22 °C
Procedure
To a stirred solution of (1R,2S)-2-(but-3-en-1-yl)cyclopentanol (see International Patent Application Publication No. WO2009/134624) (2.1 g) and DIPEA (5.3 mL) in anhydrous 1,4-dioxane (51 ml), at 10° C. and under nitrogen, was added a solution of triphosgene (1.5 g) in dioxane (51 ml). This reaction was stirred at 22° C. for 1.5 hour and 3-methyl-L-valine (2 g) and NaOH (1M, 30.5 mL) were added, then stirred at 70° C. for 15 hours. At 22° C., the reaction solution was acidified to pH 3 with 1 N HCl and extracted with (3×100 ml) ether. The combined organic layer were washed with water (100 ml), brine (70 ml), dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, eluting with 10 to 100% EtOAc in hexane) to give the desired product (3.26 g). LRMS (ES+) M/Z (M+Na)+ 320.1.
Workup
- stirringstirred at 70° C. for 15 hours
- customAt 22° C.
- extractionextracted with (3×100 ml) ether
- washThe combined organic layer were washed with water (100 ml), brine (70 ml)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (silica gel, eluting with 10 to 100% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-55cae77396fb47c09a37a721fb4d2762
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328138B2
Reaction notes
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