HCID 69607339, compound → HCID 69607378, compound

HRID 1244105Notes

Reaction equation

HRID 1244105 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([CH2:24][CH:25]=[CH2:26])([OH:23])[CH2:20]C=C)=[CH:13][CH:12]=2)=[C:9]([Cl:27])[S:8][C:7]=1[NH:28][C:29](=[O:33])[CH2:30][C:31]#[N:32])=[O:5])[CH3:2]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]3([OH:23])[CH2:20][CH:26]=[CH:25][CH2:24]3)=[CH:15][CH:16]=2)=[C:9]([Cl:27])[S:8][C:7]=1[NH:28][C:29](=[O:33])[CH2:30][C:31]#[N:32])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 69607339HCID 69607339, compound

Product 1

HCID 69607378HCID 69607378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ambient solution of 4-[4-(2-allyl-2-hydroxy-pent-4-enyloxy)-phenyl]-5-chloro-2-(2-cyano-acetylamino)-thiophene-3-carboxylic acid ethyl ester (300 mg, 0.613 mmol) in DCM (12.3 mL) was added [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinynlidene)dichloro(phenylmethylene)-(tricyclohexylphoshine)ruthenium] (29 mg, 0.034 mmol) in a single portion. The reaction was stirred overnight and then concentrated under reduced pressure to a dark oil. The residue was purified by MPLC (SiO2 gel, 1:1 Hx:EtOAc) to yield the title compound as an oil. MS (ESI) m/e 459 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.88 (m, 3H), 2.32 (d, J=15.60 Hz, 2H), 2.56 (d, J=15.60 Hz, 2H), 3.91 (s, 2H), 4.01 (m, 2H), 4.31 (m, 2H), 4.90 (s, 1H), 5.67 (s, 2H), 6.98 (m, 2H), 7.14 (m, 2H), 11.37 (s, 1H).

Workup

  1. concentrationconcentrated under reduced pressure to a dark oil
  2. customThe residue was purified by MPLC (SiO2 gel, 1:1 Hx:EtOAc)

Sources & evidence

ORD record
ord-c615e42789ab407582cd910a63637ab9
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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