Hexane → HCID 11504338, compound

HRID 735251Notes

Reaction equation

HRID 735251 reaction equation
CO[C:3](=[O:32])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:31])[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:18]([Br:30])[CH:17]=1)[CH3:15].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CCCCCC>CCOC(C)=O>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2([CH3:15])[C:3](=[O:32])[C:4]3[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][C:9]=3[Cl:10])[NH:12][C:13]2=[O:31])=[CH:17][C:18]=1[Br:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 2733832Lithium HexamethyldisilazideHCID 68819438HCID 68819438, compound

Product 1

HCID 11504338HCID 11504338, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 1, using a 2-[2-(4-benzyloxy-3-bromo-phenyl)-propionylamino]-4,6-dichloro-benzoic acid methyl ester (0.80 g, 1.50 mmol) and LiHMDS (3.20 mmol, 1M THF solution). After normal workup, the objective compound (0.51 g, 67%) was obtained as white solid by a flash column chromatography (n-hexane:EtOAc=5:1): 1H NMR (200 MHz, CDCl3) δ 1.71 (s, 3H, CH3), 5.09 (s, 2H, CH2Ph), 6.78 (d, J=2.0 Hz, 1H, ArH), 6.85 (d, J=9.0 Hz, 1H, ArH), 7.04 (dd, J=8.6, 2.4 Hz, 1H, ArH), 7.11 (d, J=2.4 Hz, 1H, ArH), 7.33-7.43 (m, 5H, ArH); m.p. 189-190° C.; MS(EI) m/e 503 [M+], 91; HRMS m/e cacld. for C23H16NO3Br1Cl2 502.9691, found 502.9696.

Workup

  1. customThe objective compound was prepared by the same procedure for the example 1

Sources & evidence

ORD record
ord-2aabdd7792b64c358b9c212554a53558
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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