Tetrahydrofuran → HCID 86634382, compound

HRID 1191282Notes

Reaction equation

HRID 1191282 reaction equation
[N:1]1([C:8]2[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])[CH:17]3[CH2:32][CH2:33][N:34]=[N+]=[N-])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[NH2:34][CH2:33][CH2:32][CH:17]1[CH:16]([NH:15][C:10]2[N:9]=[C:8]([N:1]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:13]=[C:12]([Cl:14])[N:11]=2)[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 86634380HCID 86634380, compound

Product 1

HCID 86634382HCID 86634382, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound 17 (75.5 mg), tetrahydrofuran (2 mL) and triphenylphosphine (46.3 mg) were stirred at room temperature for 1 day and then added water (0.01 mL). The reaction solution was heated at reflux for 1 day and then concentrated. The residue was purified by silica gel column chromatography (dichloromethane:methanol:triethylamine=90:10:1) to obtain the title compound (55.5 mg) having the following physical properties.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureat reflux for 1 day
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol:triethylamine=90:10:1)

Sources & evidence

ORD record
ord-de53385bf4a04d57b01620e37a041215
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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