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

HRID 2301472Notes

Reaction equation

[C:1]([NH:4][C:5]([CH2:16][C:17]1[S:18][CH:19]=[C:20]([C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:21]=1)(C(OCC)=O)[C:6](OCC)=[O:7])(=[O:3])[CH3:2].[BH4-].[Li+].O1CCCC1>O1CCCC1>[C:22]([C:20]1[CH:21]=[C:17]([CH2:16][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6][OH:7])[S:18][CH:19]=1)#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

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-b96366a0965646dfacf61f3b8642d54d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500849B1

Reaction notes

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