Decanoic Acid → HCID 86653231, compound

HRID 2360350Notes

Reaction equation

HRID 2360350 reaction equation
[C:1]([C@@H:3]([NH:5][C:6](=[O:12])OC(C)(C)C)[CH3:4])#[N:2].[C:13](O)(=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]C>>[C:1]([C@@H:3]([NH:5][C:6](=[O:12])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH3:4])#[N:2]

Participants

3

Reactant 2

HCID 2969Decanoic AcidHCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamate

Product 1

HCID 86653231HCID 86653231, compoundYield 54.3%

Procedure

General procedure D was used to deprotect 0.160 g (0.94 mmols) of 4. The product was immediately carried on using general procedure F and coupled to decanoic acid (0.94 mmol, 0.162 g). The product was purified via flash chromatography to yield 0.115 g (0.51 mmols) of the title product. 1H NMR (300 MHz, CDCl3) δ 6.07 (s, 1H), 4.94 (dq, J=7.2, 14.5, 1H), 2.26-2.16 (m, 2H), 1.69-1.58 (m, 2H), 1.54 (d, J=7.2, 3H), 1.26 (d, J=6.4, 12H), 0.86 (t, J=6.7, 3H).

Workup

  1. customThe product was purified via flash chromatography

Sources & evidence

ORD record
ord-4bbe3d4b08ae43268958f6b1a7114af0
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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