Tetrahydrofuran → HCID 69009230, compound

HRID 1191277Notes

Reaction equation

HRID 1191277 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([NH:19][CH:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH:21]1[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:18])([CH3:15])([CH3:14])[CH3:13].O1CCCC1.C(N(CC)CC)C>O>[C:12]([O:16][C:17]([NH:19][CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH:21]1[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 20806985HCID 20806985, compound

Product 1

HCID 69009230HCID 69009230, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Benzyloxycarbonyl chloride (2.55 mL) was added dropwise to the compound 12 (3.40 g), tetrahydrofuran (50 mL) and triethylamine (4.15 mL) with stirring at 0° C. The reaction solution was stirred at 0° C. for 20 minutes, added water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1) to obtain the title compound (4.81 g) having the following physical properties.

Workup

  1. stirringThe reaction solution was stirred at 0° C. for 20 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

Sources & evidence

ORD record
ord-f9594c3be6394cab94d80e11c3ae8b1a
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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