Lithium Hexamethyldisilazide → HCID 11601657, compound

HRID 735238Notes

Reaction equation

HRID 735238 reaction equation
CO[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH:11][C:12](=[O:21])[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>CCOC(C)=O>[Cl:10][C:7]1[CH:6]=[C:5]2[C:4]([C:3](=[O:22])[C:13]([CH3:14])([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:12](=[O:21])[NH:11]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 68818273HCID 68818273, compound

Product 1

HCID 11601657HCID 11601657, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 1, using a 4-chloro-2-(2-phenyl-propionyl amino)-benzoic acid methyl ester (1.00 g, 3.15 mmol) and LiHMDS (9.44 mmol, 1M solution in THF). After normal workup, the pure objective compound (0.54 g, 60%) was obtained as pale yellow solid by a flash column chromatography (Hex:EtOAc=4:1): 1H NMR (200 MHz, CDCl3) δ 1.86 (s, 3H, CH3), 6.94 (d, J=1.63 Hz, 1H, ArH), 7.06 (dd, J=8.55 Hz, 1.63 Hz, 1H, ArH), 7.26-7.32 (m, 5H, ArH), 7.83 (d, J=8.14 Hz, 1H, ArH), 9.21 (br s, 1H, NH); m.p. 174-175° C.; MS(EI) m/e 285 [M+], 153, 132, 104; HRMS m/e cacld. for C16H12NO2Cl 285.0557, found 285.0552.

Workup

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

Sources & evidence

ORD record
ord-d5e17f02c32d4230b8c032cbee249127
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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