ChemicalBook CAS DataBase List biotinylamidoethylacetamide

biotinylamidoethylacetamide synthesis

6synthesis methods

Product Name:biotinylamidoethylacetamide
CAS Number:111790-37-5
Molecular formula:C12H22N4O2S
Molecular Weight:286.39

57260-73-8
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35013-72-0 Synthesis

35013-72-0
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111790-37-5
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$50.00/25 mg

Yield: 78%

Reaction Conditions:

Stage #1:N-BOC-1,2-diaminoethane;biotin N-Hydroxysuccinimide ester in N,N-dimethyl-formamide at 20;
Stage #2: with hydrogenchloride in 1,4-dioxane;methanol

Steps:

1 iV-(2-aminoethyl)-5-(2-oxo-l,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanamide (22)
Neat tert-butyl A^r-(2-aminoethyl)carbamate was added to a suspension of NHS-ester 21 in anhydrous DMF (8.0 mL) and the reaction stirred at rt overnight. Upon consumption of starting material EtzO was flowed in the mixture chilled to -20 °C overnight. The resultant precipitate was collected via vacuum filtration and dried under suction to yield Boc-protected amine (1.18 g, 78%) as a white powder. The intervening carbamate was stirred in MeOH containing 4M HC1 to provide the amine after evaporation of the solvent, which was taken on without further purification. ^lH NMR (500 MHz, DMSO-d⁶) d 6.45 (s, 1H), 6.39 (s, 1H), 4.30 (dd, J= 7.7, 5.1 Hz, 1H), 4.13 (ddd,J= 7.8, 4.4, 1.9 Hz, 1H), 3.28 (q, J= 6.2 Hz, 2H), 3.10 (ddd,J= 8.6, 6.1, 4.4 Hz, 1H), 2.86 - 2.78 (0269) (m, 3H), 2.57 (d, J= 12.4 Hz, 1H), 2.10 (t, J= 7.5 Hz, 2H), 1.65 - 1.41 (m, 4H), 1.39 - 1.22 (m, 2H). ¹³C NMR (125 MHz, DMSO-d⁶) d 172.78, 162.75, 61.05, 59.22, 55.42, 38.59, 36.39, 35.16, 28.26, 28.08, 25.03.

References:

THE UNIVERSITY OF CHICAGO WO2021/55960, 2021, A1 Location in patent:Page/Page column 73; 81-82

35013-72-0 Synthesis

35013-72-0
360 suppliers
$12.00/100mg