Triphenylphosphine → HCID 67377783, compound

HRID 1747469Notes

Reaction equation

HRID 1747469 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12].[CH2:15]([O:17][C:18](=[O:34])[CH2:19][CH:20]([N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[NH:26][C:25]1=[O:33])[CH2:21][CH2:22][CH3:23])[CH3:16].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>O1CCCC1>[CH2:15]([O:17][C:18](=[O:34])[CH2:19][CH:20]([N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([O:10][C:11]([F:14])([F:13])[F:12])[CH:4]=2)[C:25]1=[O:33])[CH2:21][CH2:22][CH3:23])[CH3:16]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 594972633-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 59497457HCID 59497457, compound

Product 1

HCID 67377783HCID 67377783, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Amino-3-trifluoromethoxy-phenyl)-methanol (100 mg, 0.48 mmol) and 3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (133 mg, 0.48 mmol) is taken up in 4 mL of tetrahydrofuran and then triphenyl phosphine is added (190 mg, 0.72 mmol). The reaction is stirred at room temperature and DIAD (141 μL, 0.72 mmol) is, added dropwise to the reaction. The reaction is stirred at room temperature for 1 hour and then the solvent evaporated in vacuo. Product is purified by preprative HPLC 30%-90% acetonitrile/water to give the title compound (20 mg, 0.04 mmol 9%). LCMS (ESMS): m/z 466.1 (M+H+).

Workup

  1. additionadded dropwise to the reaction
  2. stirringThe reaction is stirred at room temperature for 1 hour
  3. customthe solvent evaporated in vacuo
  4. customProduct is purified by preprative HPLC 30%-90% acetonitrile/water

Sources & evidence

ORD record
ord-9d9d2b4a6ab94a60a93952abbde382ad
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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