2-Benzyloxycarbonylamino-4-methoxycarbonylphenyl trifluoromethanesulfonate → Methyl 3-benzyloxycarbonylamino-4-(4-methyl-1-pentynyl)benzoate

HRID 278067Notes

Reaction equation

HRID 278067 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][C:8]=1[NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])(=O)=O.[CH3:30][CH:31]([CH3:48])[CH2:32][C:33]#[C:34][Sn](CCCC)(CCCC)CCCC>>[CH2:21]([O:20][C:18]([NH:17][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:7]=1[C:34]#[C:33][CH2:32][CH:31]([CH3:48])[CH3:30])[C:13]([O:15][CH3:16])=[O:14])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 226274432-Benzyloxycarbonylamino-4-methoxycarbonylphenyl trifluoromethanesulfonateHCID 85703892(4-Methyl-1-pentynyl)(tributyl)stannane

Product 1

HCID 22627249Methyl 3-benzyloxycarbonylamino-4-(4-methyl-1-pentynyl)benzoateYield 88.9%

Procedure

Methyl 3-benzyloxycarbonylamino-4-(4-methyl-1-pentynyl)benzoate (2.25 g) was prepared from 2-benzyloxycarbonylamino-4-methoxycarbonylphenyl trifluoromethanesulfonate (3.0 g) and (4-methyl-1-pentynyl)(tributyl)stannane (2.7 g) in a similar manner to that of Preparation 1 (2).

Sources & evidence

ORD record
ord-62794db6788f41b8b78ef71517a84523
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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