Triphenylphosphine → HCID 11354321, compound

HRID 2373832Notes

Reaction equation

HRID 2373832 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([Br:33])[CH:30]=[CH:29][C:28]=1[OH:34])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:8][CH:7]=1.[N:37]1([CH2:43][CH2:44]O)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]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.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([Br:33])[CH:30]=[CH:29][C:28]=1[O:34][CH2:44][CH2:43][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5363146Diisopropyl azodicarboxylateHCID 11466926HCID 11466926, compound

Product 1

HCID 11354321HCID 11354321, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S)-(5-bromo-2-hydroxy-benzoylamino)-3-(2′-phenoxy-biphenyl-4-yl)-propionic acid methyl ester (25 mg, 46 μmol, obtained by following similar procedure described for example 34), 2-morpholin-4-yl-ethanol (1.5 eq., 8.3 μL, 69 μmol) and triphenylphosphine (1.5 eq., 18 mg, 69 μmol) in anhydrous THF (1 mL) was treated with DIAD (1.5 eq., 13.5 μl, 69 μmol) as described in Procedure I. Flash column chromatography (4:1 hexanes:EtOAc) provided 13 mg of the title compound. LCMS for C35H35BrN2O6: 659, 661.

Sources & evidence

ORD record
ord-612e35ad6d874e07a81e9977c8da7a67
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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