Triphenylphosphine → HCID 178489997, compound

HRID 1627297Notes

Reaction equation

HRID 1627297 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:35]([F:36])=[CH:34][C:28]([O:29][CH2:30][CH2:31][CH2:32]O)=[CH:27][C:26]=3[F:37])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:38][CH3:39].[C:40]([O:44][C:45]([NH:47][C:48]([NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[NH:49])=[O:46])([CH3:43])([CH3:42])[CH3:41].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:54]([O:53][C:51](=[O:52])[N:50]=[C:48]([NH:47][C:45]([O:44][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:46])[NH:49][CH2:32][CH2:31][CH2:30][O:29][C:28]1[CH:34]=[C:35]([F:36])[C:25]([CH2:24][S:23][C:14]2[N:15]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:11]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:38][CH3:39])[CH:4]=3)([CH3:9])[CH3:10])=[CH:12][N:13]=2)=[C:26]([F:37])[CH:27]=1)([CH3:57])([CH3:56])[CH3:55]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 66740953HCID 66740953, compoundHCID 135638421tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamate

Product 1

HCID 178489997HCID 178489997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner described previously, a mixture of 3-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)propan-1-ol (330 mg, 0.57 mmol), 1,3-bis(tert-butoxycarbonyl)guanidine (266 mg, 1.02 mmol), PPh3 (225 mg, 0.85 mmol) and DIAD (177 μL, 0.85 mmol) was reacted in THF, processed and purified by flash chromatography (80% EtOAc/Hex) to give tert-butyl(tert-butoxycarbonylamino)(3-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)propylamino)methylenecarbamate. MS (EI) m/z 818.6 (MH+).

Workup

  1. custompurified by flash chromatography (80% EtOAc/Hex)

Sources & evidence

ORD record
ord-d97d51afe81e4655b3d691598db95aab
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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