Methyl 8-chloro-8-oxooctanoate → methyl 8-[{4-[(4-butylphenyl)ethynyl]benzyl}(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]-8-oxooctanoate

HRID 733551Notes

Reaction equation

HRID 733551 reaction equation
Cl.[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:34]=[CH:33][C:17]([CH2:18][NH:19][C:20]3[CH:32]=[CH:31][C:23]4[O:24][C:25]([CH3:30])([CH3:29])[O:26][C:27](=[O:28])[C:22]=4[CH:21]=3)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].Cl[C:36](=[O:47])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44]>>[CH2:2]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:14]2[CH:34]=[CH:33][C:17]([CH2:18][N:19]([C:20]3[CH:32]=[CH:31][C:23]4[O:24][C:25]([CH3:30])([CH3:29])[O:26][C:27](=[O:28])[C:22]=4[CH:21]=3)[C:36](=[O:47])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])=[CH:16][CH:15]=2)=[CH:10][CH:11]=1)[CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 4586585Methyl 8-chloro-8-oxooctanoateHCID 684196986-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one hydrochloride

Product 1

HCID 57841326methyl 8-[{4-[(4-butylphenyl)ethynyl]benzyl}(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]-8-oxooctanoate

Procedure

The titled compound was prepared following the procedure J using 6-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one hydrochloride and methyl 8-chloro-8-oxooctanoate as a colorless oil (97%). 1H NMR (CDCl3, 300 MHz) δ 7.69 (br s, 1H), 7.44 (m, 4H), 7.18 (m, 4H), 7.04 (m, 1H), 6.92 (d, J=8.7 Hz, 1H), 4.88 (s, 2H), 3.66 (s, 3H). 2.63 (t, J=7.5 Hz, 2H), 2.28 (t, J=7.3 Hz, 2H), 2.05 (t, J=7.3 Hz, 2H), 1.75 (s, 6H), 1.61 (m, 6H), 1.38 (m, 2H), 1.26 (m, 4H), 0.94 (t, J=7.3 Hz, 3H). M+ (ESI): 610.2. HPLC, Rt: 5.81 min (Purity: 100%).

Sources & evidence

ORD record
ord-5880b66447a2416491b0f3fcca340d6e
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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