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

HRID 81863Notes

Reaction equation

HRID 81863 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Sources & evidence

ORD record
ord-1300a00375354214a659e43496df8a9a
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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