Stannane, tributyl(1-methylethenyl)- → HCID 68973673, compound

HRID 1272696Notes

Reaction equation

HRID 1272696 reaction equation
[CH3:1][O:2][C:3](=[O:42])[C@@H:4]([NH:12][C:13]([C:15]1[N:16]=[C:17]([CH2:36][CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=1)=[CH:20][CH:19]=2)=[O:14])[CH2:5][C:6]1[S:7][C:8](Br)=[CH:9][CH:10]=1.[CH2:43]([Sn](CCCC)(CCCC)C(C)=C)[CH2:44][CH2:45]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:42])[C@@H:4]([NH:12][C:13]([C:15]1[N:16]=[C:17]([CH2:36][CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=1)=[CH:20][CH:19]=2)=[O:14])[CH2:5][C:6]1[S:7][C:8]([C:44]([CH3:45])=[CH2:43])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10871254Stannane, tributyl(1-methylethenyl)-HCID 68972631HCID 68972631, compound

Product 1

HCID 68973673HCID 68973673, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-(5-Bromo-thiophen-2-yl)-2(S)-{[6-(4-tert-butyl-phenoxy)-1-cyclopentylmethyl-isoquinoline-3-carbonyl]-amino}-propionic acid methyl ester (prepared in Example 38) was treated with tributyl-isopropenyl-stannane and Pd(PPh3)4 as described in the general procedure M to afford 2(S)-{[6-(4-tert-butyl-phenoxy)-1-cyclopentylmethyl-isoquinoline-3-carbonyl]-amino}-3-(5-isopropenyl-thiophen-2-yl)-propionic acid methyl ester. This was treated with Pd/C and H2 (1 atm) by the general procedure N to afford 2(S)-{[6-(4-tert-butyl-phenoxy)-1-cyclopentylmethyl-isoquinoline-3-carbonyl]-amino}-3-(5-isopropyl-thiophen-2-yl)-propionic acid methyl ester. This ester was hydrolyzed by the general procedure C to afford the title compound.

Sources & evidence

ORD record
ord-0c516c659fa04a99b51f30105677e697
Source dataset
uspto-grants-2007_04
Patent number
US07208601B2

Reaction notes

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