Methyl 2-{methyl[(4-methylphenyl)sulfonyl]amino}acetate → Benzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate

HRID 81863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81863
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=2)[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][N:35]([CH2:46][C:47](OC)=[O:48])[S:36]([C:39]1[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=1)(=[O:38])=[O:37]>>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=2)[C:47](=[O:48])[CH2:46][N:35]([CH3:34])[S:36]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 3277444Methyl 2-{methyl[(4-methylphenyl)sulfonyl]amino}acetateHCID 68076436Benzyl 2-(Benzyloxy)-4-(4-Bromobenzylamino)Benzoate

Produkt 1

HCID 66728422Benzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoateAusbeute 90 %

Versuchsvorschrift

Secondary aniline 2 was coupled to carboxylic acid 6 on a 0.2 mmol scale via General Procedure B to furnish 9 (167 mg, 90%): δH (400 MHz, CDCl3) 2.33 (s, 3H, CH3Ar), 2.73 (s, 3H, CH3Ar), 3.54 (s, 2H, CH2CO), 4.64 (s, 2H, CH2Ar), 4.99 (s, 2H, CH2Ar), 5.28 (s, 2H, CH2Ar), 6.50 (br s, 1H, CH (Ar)), 6.55 (dd, J=8.3 and 1.8 Hz, 1H, CH (Ar)), 6.88 (d, J=8.3 Hz, 2H, 2 CH (Ar)), 7.16-7.34 (m, 14H, 14 CH (Ar)), 7.51 (d, J=8.3 Hz, 2H, 2 CH (Ar)), 7.75 (d, J=8.3 Hz, 1H, CH (Ar)); δC (100 MHz, CDCl3) 21.4, 29.6, 36.0, 51.2, 52.4, 53.3, 66.9, 70.7, 113.9, 119.8, 120.9, 121.7, 126.9, 127.3, 127.9, 128.2, 128.5, 129.4, 130.5, 131.6, 133.1, 135.2, 135.5, 135.6, 135.7, 143.3, 144.7, 158.7, 165.2, 167.0; LRMS (ES+) Calcd for [C38H35BrN2O6S+H] 727.15 found 726.83.

Quellen und Nachweise

ORD-Eintrag
ord-1300a00375354214a659e43496df8a9a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846707B2

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