Triethylamine → tert-Butyl methyl[2-(methyl{[3-methyl-5-(methylamino)thiophen-2-yl]carbonyl}amino)ethyl]carbamate

HRID 446589Notes

Reaction equation

HRID 446589 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:30])[CH2:9][CH2:10][N:11]([CH3:29])[C:12]([C:14]1[S:18][C:17](CNC(=O)OC(C)(C)C)=[CH:16][C:15]=1[CH3:28])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:31]([N:33](CC)CC)C.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[CH3:30][N:8]([CH2:9][CH2:10][N:11]([CH3:29])[C:12]([C:14]1[S:18][C:17]([NH:33][CH3:31])=[CH:16][C:15]=1[CH3:28])=[O:13])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86663472tert-Butyl {5-[{2-([tert-butoxycarbonyl)(methyl)amino]ethyl}(methyl)carbamoyl]-4-methylthiophen-2-yl}methylcarbamate

Product 1

HCID 86663473tert-Butyl methyl[2-(methyl{[3-methyl-5-(methylamino)thiophen-2-yl]carbonyl}amino)ethyl]carbamateYield 99%

Procedure

The compound (418 mg, 0.947 mmol) obtained in Example 90a, triethylamine (0.658 mL, 4.74 mmol) and di-tert-butyl dicarbonate (248 mg, 1.14 mmol) were used to give the title compound (319 mg; yield, 99%) as a yellow oily substance according to the method described in Example 89c.

Sources & evidence

ORD record
ord-b0fb8a4ddaf540249b643da6edeccdeb
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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