Pyridine → HCID 12148460, compound

HRID 2414391Notes

Reaction equation

HRID 2414391 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH:29]=[CH:30][CH:31]=1)[CH2:10][O:11][CH2:12][C@@H:13]([NH:16][C:17](=[O:28])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=1)[NH2:19])[C:14]#[N:15])=[O:6])[CH:2]=[CH2:3].[F:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH:29]=[CH:30][CH:31]=1)[CH2:10][O:11][CH2:12][C@@H:13]([NH:16][C:17](=[O:28])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=1)[NH:19][C:36]1[CH:37]=[CH:38][C:33]([F:32])=[CH:34][CH:35]=1)[C:14]#[N:15])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2856454-Fluorophenylboronic acidHCID 12148457HCID 12148457, compound

Product 1

HCID 12148460HCID 12148460, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-[2-[3-(allyloxycarbonyl)-benzyloxy]-1(S)-cyanoethyl]-3-methyl-L-phenylalaninamide (0.6 g, 1.42 mmol) in CH2Cl2 (15 mL) is added 4-fluorophenylboronic acid (0.398 g, 2.85 mmol), cupric acetate (0.26 g, 1.4 mmol) and pyridine (0.23 mL, 2.85 mmol), and the dark blue solution is stirred overnight at room temp. The solution is then diluted with CH2Cl2 (35 mL), and washed with 1 N HCl (50 mL) and brine (50 mL), then dried (MgSO4), evaporated and chromatographed (silica, 30% EtOAc/hexane) to yield N-[2-[3-(allyloxycarbonyl)-benzyloxy]-1(S)-cyanoethyl]-3-methyl-Nα-(4-fluorophenyl)-L-phenylalaninamide, as a clear oil.

Workup

  1. washwashed with 1 N HCl (50 mL) and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customchromatographed (silica, 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-dc78621fd4ca41d49f2ba4add402febd
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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