Hexane → HCID 11522001, compound

HRID 735259Notes

Reaction equation

HRID 735259 reaction equation
CO[C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:22])[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH3:13].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CCCCCC>CCOC(C)=O>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]2([CH3:13])[C:3](=[O:23])[C:4]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:10][C:11]2=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 2733832Lithium HexamethyldisilazideHCID 68817753HCID 68817753, compound

Product 1

HCID 11522001HCID 11522001, compoundYield 57%

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-methoxy-phenyl)-propionyl amino]-benzoic acid methyl ester (1.00 g, 3.19 mmol) and LiHMDS (9.57 mmol, 1M solution in THF). After normal workup, the objective compound (0.51 g, 57%) was obtained as yellow solid by a flash column chromatography (n-hexane:EtOAc=5:1): 1H NMR (200 MHz, CDCl3) δ 1.83 (s, 3H, CH3), 3.73 (s, 3H, OCH3), 6.77 d, J=8.9 Hz, 2H, ArH), 6.89-7.07 (m, 2H, ArH), 7.21 (d, J=8.9 Hz, 2H, ArH), 7.44-7.89 (m, 2H, ArH), 9.08 (br s, 1H).

Workup

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

Sources & evidence

ORD record
ord-3f4f7a899fe345ec8b996b9076e6e5d3
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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