Pyridine → toluene-4-thiosulfonic acid S-(4,5-bis-tert-butoxycarbonylamino-2-tert-butyl-phenyl)ester

HRID 23490Notes

Reaction equation

HRID 23490 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[C:12]([SH:14])[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:10][C:9]=1[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:4])([CH3:3])[CH3:2].[S:28](Br)([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29].N1C=CC=CC=1>CCOC(C)=O>[C:23]([O:22][C:20]([NH:19][C:9]1[C:8]([NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:27])=[CH:13][C:12]([S:14][S:28]([C:31]2[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=2)(=[O:30])=[O:29])=[C:11]([C:15]([CH3:16])([CH3:17])[CH3:18])[CH:10]=1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 54379200(2-tert-Butoxycarbonylamino-4-tert-Butyl-5-mercapto-phenyl)-carbamic Acid Tert-Butyl Ester

Product 1

HCID 69756247toluene-4-thiosulfonic acid S-(4,5-bis-tert-butoxycarbonylamino-2-tert-butyl-phenyl)ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to the General Method 15 using (2-tert-butoxycarbonylamino-4-tert-butyl-5-mercapto-phenyl)-carbamic acid tert-butyl ester (prepared in Example TT-2; 16.9 g, 42.8 mmol), tosyl bromide (10.04 g, 42.76 mmol), pyridine (10 mL), and EtOAc (150 mL). The crude product was purified by flash chromatography (5%-60% EtOAc in hexanes as eluents). 1H-NMR (CDCl3): δ 1.19 (s, 9H), 1.53 (s, 18H), 2.42 (s, 3H), 6.42 (br s, 1H), 7.22 (d, 2H), 7.28 (s, 1H), 7.5 (m, 3H), 7.87 (br s, 1H).

Workup

  1. customThe crude product was purified by flash chromatography (5%-60% EtOAc in hexanes as eluents)

Sources & evidence

ORD record
ord-5aed4de9854645f991bdac1de12bfd1e
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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