Stannane, tributyl(1-methylethenyl)- → HCID 68972732, compound

HRID 1272688Notes

Reaction equation

HRID 1272688 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[S:7][C:8](Br)=[CH:9][CH:10]=1.[CH2:21]([Sn](CCCC)(CCCC)C(C)=C)[CH2:22][CH2:23]C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[S:7][C:8]([C:22]([CH3:23])=[CH2:21])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10871254Stannane, tributyl(1-methylethenyl)-HCID 68972961HCID 68972961, compound

Product 1

HCID 68972732HCID 68972732, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

15.0 g (41.17 mmol) of 3-(5-bromo-thiophen-2-yl)-2(R)-tert-butoxycarbonylamino-propionic acid methyl ester was treated with tributyl-isopropenyl-stannane (17.88 g, 54.07 mmol) and Pd(PPh3)4 (4.8 g, 4.15 mmol) as described in the general procedure M to afford 8.50 g of 2(R)-tert-butoxycarbonylamino-3-(5-isopropenyl-thiophen-2-yl)-propionic acid methyl ester.

Sources & evidence

ORD record
ord-cd87c3eb6d57433aa269e99377d2209f
Source dataset
uspto-grants-2007_04
Patent number
US07208601B2

Reaction notes

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