Diethyl(acetamido)[[4-(1-dodecynyl)-2-thienyl]methyl]propanedioate → N-[1-[4-(1-dodecynyl)-2-thienyl]-3-hydroxy-2-propyl]acetamide

HRID 375933Notes

Reaction equation

C([O:3][C:4](=O)[C:5]([NH:29][C:30](=[O:32])[CH3:31])([CH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:16]=1)C(OCC)=O)C.[BH4-].[Li+].O1CCCC1>O1CCCC1>[C:17]([C:15]1[CH:16]=[C:12]([CH2:11][CH:5]([NH:29][C:30](=[O:32])[CH3:31])[CH2:4][OH:3])[S:13][CH:14]=1)#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of diethyl(acetamido)[[4-(1-dodecynyl)-2-thienyl]methyl]propanedioate (12.3 g) in dry tetrahydrofuran (100 ml) was added 2M lithium borohydride/tetrahydrofuran (12.8 ml), and the mixture was stirred at 60° C. for 4 hrs. The solution was cooled, quenched with a 50:50:10 solution of methanol:water:acetic acid, and extracted with ethyl acetate. The organic extracts were evaporated, and the residue was chromatographed on silica gel (9:1 ethyl acetate:dichloromethane). The appropriate fractions were collected and evaporated. The residue was crystallized from ether:heptane to give 5.3 g (57%) of product, mp 55°-58° C.

Workup

temperatureThe solution was cooled
customquenched with a 50:50:10 solution of methanol
extractionwater:acetic acid, and extracted with ethyl acetate
customThe organic extracts were evaporated
customthe residue was chromatographed on silica gel (9:1 ethyl acetate:dichloromethane)
customThe appropriate fractions were collected
customevaporated
customThe residue was crystallized from ether

Sources & evidence

ORD record: ord-5237a60db5fd4f6891b55ca8b5eda77a
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488061

Reaction notes

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