Tributyl(prop-1-yn-1-yl)stannane → Methyl 3-benzyloxycarbonylamino-4-(1-propynyl)benzoate

HRID 1108691Notes

Reaction equation

HRID 1108691 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.[CH2:30]([Sn](CCCC)(CCCC)C#CC)[CH2:31][CH2:32]C>>[CH2:21]([O:20][C:18]([NH:17][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:7]=1[C:30]#[C:31][CH3:32])[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 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 226274432-Benzyloxycarbonylamino-4-methoxycarbonylphenyl trifluoromethanesulfonate

Product 1

HCID 22627370Methyl 3-benzyloxycarbonylamino-4-(1-propynyl)benzoateYield 85.5%

Procedure

Methyl 3-benzyloxycarbonylamino-4-(1-propynyl)benzoate (1.34 g) was prepared from 2-benzyloxycarbonylamino-4-methoxycarbonylphenyl trifluoromethanesulfonate (2.1 g) and tributyl(1-propynyl)stannane (2.49 g) in a similar manner to that of Preparation 1 (2).

Sources & evidence

ORD record
ord-397303f562d748e69736e837b19cd21b
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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