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

HRID 1859563Notes

Reaction equation

HRID 1859563 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[C:12]([SH:14])[C:11]([CH:15]([CH3:17])[CH3:16])=[CH:10][C:9]=1[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([CH3:4])([CH3:3])[CH3:2].[S:27](Br)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28].N1C=CC=CC=1>CCOC(C)=O>[C:22]([O:21][C:19]([NH:18][C:9]1[C:8]([NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:26])=[CH:13][C:12]([S:14][S:27]([C:30]2[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=2)(=[O:29])=[O:28])=[C:11]([CH:15]([CH3:16])[CH3:17])[CH:10]=1)=[O:20])([CH3:24])([CH3:23])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 131723783(2-tert-Butyoxycarbonylamino-4-isopropyl-5-mercapto-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 69753768Toluene-4-thiosulfonic acid S-(4,5-bis-tert-butoxycarbonylamino-2-isopropyl-phenyl) ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to the General Method 15 using (2-tert-butyoxycarbonylamino-4-isopropyl-5-mercapto-phenyl)-carbamic acid tert-butyl ester (prepared in Example TT-1; 22.1 mmol), tosyl bromide (5.2 g, 22 mmol), pyridine (5 mL), and EtOAc (50 mL). The crude product was purified by flash chromatography (5%-60% EtOAc in hexanes as eluents). 1H-NMR (CDCl3): δ0.97 (s, 6 H), 1.53 (s, 18 H), 2.4 (s, 3 H), 3.2 (m, 1 H), 7.11 (br s, 1 H), 7.22 (d, 2 H), 7.28 (s, 1 H), 7.36 (s, 1 H), 7.5 (d, 2 H), 7.75 (br s, 1 H).

Workup

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

Sources & evidence

ORD record
ord-b41932390be24ef7bbccefeb369fe5a7
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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