Water → 5-[1-(3-Phenyl-allyl)-1H-imidazol-4-yl]-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid ethyl ester

HRID 852863Notes

Reaction equation

HRID 852863 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH:5]=[CH:6][CH:7]([NH:14][C:15](=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:8][C:9]1[N:10]=[CH:11][NH:12][CH:13]=1)[CH3:2].[H-].[Na+].[CH2:32](Br)[CH:33]=[CH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O>CN(C=O)C.C(#N)C>[CH2:1]([O:3][C:4](=[O:29])[CH:5]=[CH:6][CH:7]([NH:14][C:15](=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:8][C:9]1[N:10]=[CH:11][N:12]([CH2:32][CH:33]=[CH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:13]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 178471313HCID 178471313, compound

Product 1

HCID 694153655-[1-(3-Phenyl-allyl)-1H-imidazol-4-yl]-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid ethyl esterYield 68.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

The 5-(1H-Imidazol-4-yl)-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid ethyl ester (100 mg, 0.25 mmol) in DMF (1 mL) was treated with NaH (10 mg, 60%, 0.25 mmol) at room-temperature. After 5 minutes cinnamyl bromide (50 mg, 0.25 mmol) was added, and the solution stirred overnight. Analytical HPLC showed the product was a 60:40 mixture of τ (required) and π (undesired) isomers respectively. The solution as taken up into water and acetonitrile and subject to reverse phase HPLC (30% B to 100% B over 25 min). The product, a mixture of both isomers, was obtained as an oil (88 mg, 68%), ESMS 514 (M+H+). 13C NMR δ 174.72, 174.67, 174.22, 171.69, 170.52, 166.20, 145.85, 142.93, 138.31, 138.16, 137.81, 137.45, 134.89, 134.81, 133.37, 132.86, 131.49, 131.39, 129.26, 128.98, 128.52, 128.34, 127.04, 125.68, 122.23, 119.68, 119.61, 119.54, 118.93, 114.55, 63.08, 61.90, 60.91, 60.79, 57.59, 54.77, 52.59, 52.53, 51.49, 50.21, 37.04, 36.14, 35.99, 33.44, 31.44, 29.61, 29.18, 29.13, 29.03, 28.97, 25.67, 25.62, 25.46, 14.27, 14.05.

Workup

  1. customphase HPLC (30% B to 100% B over 25 min)
  2. additionThe product, a mixture of both isomers

Sources & evidence

ORD record
ord-d1a58444f72c4edbbf5d951111c05e80
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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