Hexane → HCID 11659391, compound

HRID 735257Notes

Reaction equation

HRID 735257 reaction equation
CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:23])[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([O:21][CH3:22])[CH:15]=1)[CH3:13].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CCCCCC>CCOC(C)=O>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2([CH3:13])[C:3](=[O:24])[C:4]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:10][C:11]2=[O:23])=[CH:15][C:16]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 8058HexaneHCID 2733832Lithium HexamethyldisilazideHCID 68815664HCID 68815664, compound

Product 1

HCID 11659391HCID 11659391, compoundYield 51%

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-hydroxy-3-methoxy-phenyl)-propionyl amino]-benzoic acid methyl ester (1.00 g, 3.04 mmol) and LiHMDS (9.12 mmol, 1M solution in THF). After normal workup, the objective compound (0.46 g, 51%) was obtained as yellow solid by a flash column chromatography (n-hexane:EtOAc=5:1): 1H NMR (200 MHz, CDCl3) δ 1.81 (s, 3H, CH3), 3.83 (s, 3H, OCH3), 5.55 (br s, 1H, OH), 6.76-6.87 (m, 4H, ArH), 7.12 (t, J=7.73 Hz, 1H, ArH), 7.49 (t, J=7.32 Hz, 1H, ArH), 7.90 (d, J=8.12 Hz, 1H, ArH), 8.17 (br s, 1H, NH); m.p. 168-169° C.; MS(EI) m/e 297 [M+], 178, 150; HRMS m/e cacld. for C17H15N1O4 297.1002, found 297.0999.

Workup

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

Sources & evidence

ORD record
ord-f3f4d0cf51e54a348372a3247c34e9bc
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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