4-Hexylbenzoic acid → HCID 67198379, compound

HRID 2360346Notes

Reaction equation

HRID 2360346 reaction equation
[C:1]([C@@H:3]([NH:5][C:6](=[O:12])OC(C)(C)C)[CH3:4])#[N:2].[CH2:13]([C:19]1[CH:27]=[CH:26][C:22](C(O)=O)=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>>[C:1]([C@@H:3]([NH:5][C:6](=[O:12])[C:22]1[CH:21]=[CH:20][C:19]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:27][CH:26]=1)[CH3:4])#[N:2]

Participants

3

Reactant 2

HCID 307254-Hexylbenzoic acidHCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamate

Product 1

HCID 67198379HCID 67198379, compound

Procedure

General procedure D was used to deprotect 0.210 g (1.23 mmols) of 4. The product was immediately carried on using general procedure F and coupled to 1.23 mmols of 10. The title product was purified with flash chromatography using a solvent system of ethyl acetate and hexanes (1:3) to yield 0.106 g (0.41 mmols). 1H NMR (500 MHz, CDCl3) δ 7.74-7.68 (m, 2H), 7.25 (d, J=8.2, 2H), 6.61 (s, 1H), 5.20-5.11 (m, 1H), 2.70-2.61 (m, 2H), 1.66 (t, J=6.6, 3H), 1.60 (dd, J=7.3, 14.9, 2H), 1.37-1.22 (m, 6H), 0.88 (t, J=6.8, 3H). 13C NMR (126 MHz, CDCl3) δ 173.95, 166.58, 148.00, 148.00, 131.31, 129.95, 128.78, 128.62, 127.20, 127.03, 119.42, 77.27, 77.02, 76.76, 52.57, 48.42, 36.24, 35.85, 31.63, 31.10, 28.87, 22.56, 19.57, 18.68, 14.07.

Workup

  1. customThe title product was purified with flash chromatography
  2. customto yield 0.106 g (0.41 mmols)

Sources & evidence

ORD record
ord-03a777288a5445c68b4136531065c0f4
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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