Triphenylphosphine → HCID 57718000, compound

HRID 1984824Notes

Reaction equation

HRID 1984824 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C@@H:4]([NH:13][C:14]([C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=1)=[CH:21][CH:20]=2)=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH:38]1([CH2:43]O)[CH2:42][CH2:41][CH2:40][CH2:39]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:37])[C@@H:4]([NH:13][C:14]([C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([O:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]([CH3:34])([CH3:36])[CH3:35])=[CH:31][CH:32]=1)=[CH:21][CH:20]=2)=[O:15])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:43][CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 77195CyclopentanemethanolHCID 5363146Diisopropyl azodicarboxylateHCID 57718031HCID 57718031, compound

Product 1

HCID 57718000HCID 57718000, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 50 mg (0.1 mmol) of (2S)-{[6-(4-tert-butyl-phenoxy)-isoquinoline-3-carbonyl]-amino}-3-(4-hydroxy-phenyl)-propionic acid methyl ester (Example 298) in dry THF (1 mL) was added cyclopentanemethanol (1.5 eq., 0.15 mmol, 0.016 mL), triphenylphosphine (1.5 eq., 0.15 mmol, 39 mg) and DIAD (1.5 eq., 0.15 mmol, 0.030 mL) according to the procedure M. Chromatography on silica using 20-30% ethyl acetate in hexanes afforded 27 mg of the title compound.

Sources & evidence

ORD record
ord-b5f21a0b696441618c3fff5d03831124
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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