4-Phenoxybenzoic acid → HCID 67196840, compound

HRID 2360353Notes

Reaction equation

HRID 2360353 reaction equation
[C:1]([C@@H:3]([NH:5][C:6](=[O:12])OC(C)(C)C)[CH3:4])#[N:2].[O:13]([C:20]1[CH:28]=[CH:27][C:23](C(O)=O)=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:1]([C@@H:3]([NH:5][C:6](=[O:12])[C:23]1[CH:27]=[CH:28][C:20]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:21][CH:22]=1)[CH3:4])#[N:2]

Participants

3

Reactant 2

HCID 751824-Phenoxybenzoic acidHCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamate

Product 1

HCID 67196840HCID 67196840, compound

Procedure

General procedure D was used to deprotect 1.2 mmols of 4 and immediately coupled to 1.2 mmols of 25 using general procedure F. The title product was purified by flash chromatography with ethyl acetate and hexanes to yield 0.53 mmol (0.14 g). 1H NMR (300 MHz, CDCl3) δ 7.87-7.65 (m, 3H), 7.39 (t, J=7.8, 2H), 7.20 (d, J=6.7, 1H), 7.10-6.90 (m, 5H), 6.76 (s, 2H), 5.26-5.03 (m, 1H), 1.65 (d, J=7.2, 3H).

Workup

  1. customThe title product was purified by flash chromatography with ethyl acetate and hexanes
  2. customto yield 0.53 mmol (0.14 g)

Sources & evidence

ORD record
ord-86f932bf73e640339236de2cf1f0139d
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

Loading…