Lithium Hexamethyldisilazide → HCID 11630209, compound

HRID 735237Notes

Reaction equation

HRID 735237 reaction equation
CO[C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:20])[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>CCOC(C)=O>[CH3:13][C:12]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:3](=[O:21])[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:10][C:11]1=[O:20]

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 68817246HCID 68817246, compound

Product 1

HCID 11630209HCID 11630209, compoundYield 65.4%

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-phenyl-propionyl amino)-benzoic acid methyl ester (1.00 g, 3.53 mmol) and LiHMDS (10.6 mmol, 1M THF solution). After normal workup, the pure objective compound (0.58 g, 65%) was obtained as pale yellow solid by a flash column chromatography (Hex:EtOAc=4:1): 1H NMR (200 MHz, CDCl3) δ 2.05 (s, 3H, CH3), 6.92 (d, J=8.14 Hz, 1H, ArH), 7.11 (t, J=7.73 Hz, 1H, ArH), 7.23-7.37 (m, 5H, ArH), 7.49 (t, J=7.32, 1H, ArH), 7.89 (d, J=7.73 Hz, 1H, ArH), 9.50 (br s, 1H, NH); m.p. 194-196° C.; MS(EI) m/e 251 [M+], 146, 132, 104; HRMS m/e cacld. for C16H13NO2 251.0946, found 251.0944.

Workup

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

Sources & evidence

ORD record
ord-3a63ff1a30c542f8a111758c5509af60
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

Loading…