Triphenylphosphine → HCID 59497418, compound

HRID 1747466Notes

Reaction equation

HRID 1747466 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[C:14]([Cl:19])[CH:15]=[C:16]([CH2:17]O)[C:11]=2[O:10][C:9]1=[O:20])=O)(C)(C)C.[CH2:21]([O:23][C:24](=[O:40])[CH2:25][CH:26]([N:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[NH:32][C:31]1=[O:39])[CH2:27][CH2:28][CH3:29])C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:21][O:23][C:24](=[O:40])[CH2:25][CH:26]([N:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]([CH2:17][C:16]2[C:11]3[O:10][C:9](=[O:20])[NH:8][C:12]=3[CH:13]=[C:14]([Cl:19])[CH:15]=2)[C:31]1=[O:39])[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 594972633-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 59497432HCID 59497432, compound

Product 1

HCID 59497418HCID 59497418, compoundYield 3.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Chloro-7-hydroxymethyl-2-oxo-benzooxazole-3-carboxylic acid tert-butyl ester 600 mg (2 mmol) is dissolved in tetrahydrofuran 1.5 mL and then 3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester is added (608 mg (2.2 mmol). The reaction is cooled to 0° C. and then triphenylphosphine (630 mg, 2.4 mmol) is added followed by the drop wise addition of diisopropyl azodicarboxylate (465 μL, 2.40 mmol). The reaction is stirred for 15 minutes at 0° C. and then the solvents evaporated in vacuo. The compound is purified on silica with dichloromethane methanol as the eluent. This crude material is then taken up in dichloromethane (1.5 mL) and trifluoroacetic acid (500 uL) is added drop wise to the reaction. The reaction is stirred at room temperature and monitored by LC/MS. Upon completion the reaction is evaporated in vacuo and purified by preparative reverse phase LC to give the title compound 33 mg (0.07 mmol, 3.6%). LCMS (ESMS): m/z 444.9 (M+H+).

Workup

  1. customthe solvents evaporated in vacuo
  2. customThe compound is purified on silica with dichloromethane methanol as the eluent
  3. additiontrifluoroacetic acid (500 uL) is added drop
  4. customwise to the reaction
  5. stirringThe reaction is stirred at room temperature
  6. customUpon completion the reaction is evaporated in vacuo
  7. custompurified by preparative reverse phase LC

Sources & evidence

ORD record
ord-7c70feeaf37949b4947898eb24053115
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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