HCID 59243635, compound → HCID 59243610, compound

HRID 425026Notes

Reaction equation

HRID 425026 reaction equation
[H][H].[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[S:30][C:31]([NH:37][C:38](=[O:40])[NH2:39])=[C:32]([C:34](=[O:36])[NH2:35])[CH:33]=2)=[CH:25][CH:24]=1)[C:12]([O:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].CC(O)C.C1(C)C=CC=CC=1>[C:3]([O:7][C:8]([NH:10][C@H:11]([C:12]([O:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:13])[CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[S:30][C:31]([NH:37][C:38](=[O:40])[NH2:39])=[C:32]([C:34](=[O:36])[NH2:35])[CH:33]=2)=[CH:27][CH:28]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 2

HCID 59243635HCID 59243635, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59243610HCID 59243610, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent2×

Procedure

Hydrogen gas was bubbled through a suspension of Wilkinson's catalyst (767 mg, 0.829 mmol) in IPA (10 ml) and toluene (5 ml). After 5 minutes, a solution of cyclopentyl(2S,4E)-2-[(tert-butoxycarbonyl)amino]-5-{4-[4-carbamoyl-5-(carbamoylamino)-2-thienyl]phenyl}pent-4-enoate (300 mg, 0.553 mmol) in IPA (10 ml) was added. The mixture was kept under an atmosphere of hydrogen and placed in a preheated oil bath at 80° C. After 4 hrs the reaction was judged to be complete by LC-MS. The mixture was filtered whilst still hot and the filtrate evaporated in vacuo. The residue was subjected to column chromatography eluting with 4% MeOH in DCM. Yield=120 mg, 0.198 mmol, 36% yield. LCMS purity 90%: m/z 543 [M−H]+.

Workup

  1. customplaced in a preheated oil bath at 80° C
  2. waitAfter 4 hrs the reaction was judged
  3. filtrationThe mixture was filtered whilst still hot and the filtrate
  4. customevaporated in vacuo
  5. washeluting with 4% MeOH in DCM

Sources & evidence

ORD record
ord-2af2128cb4ba47babec58f0335abb296
Source dataset
uspto-grants-2012_01
Patent number
US08106091B2

Reaction notes

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