Tetrahydrofuran → HCID 86634383, compound

HRID 1191283Notes

Reaction equation

HRID 1191283 reaction equation
[C:1](=[O:8])([O-])[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[NH2:9][CH2:10][CH2:11][CH:12]1[CH:17]([NH:18][C:19]2[N:24]=[C:23]([N:25]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:22]=[C:21]([Cl:32])[N:20]=2)[CH2:16][CH2:15][CH2:14][N:13]1[C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].O1CCCC1>O.C(N(CC)CC)C>[N:25]1([C:23]2[CH:22]=[C:21]([Cl:32])[N:20]=[C:19]([NH:18][CH:17]3[CH2:16][CH2:15][CH2:14][N:13]([C:33]([O:35][CH2:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[O:34])[CH:12]3[CH2:11][CH2:10][NH:9][C:1]([O:2][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:8])[N:24]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 4613278tert-Butyl carbonateHCID 86634382HCID 86634382, compound

Product 1

HCID 86634383HCID 86634383, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl carbonate (165 mg) was added to the compound 18 (245 mg), tetrahydrofuran (2 mL), water (2 mL) and triethylamine (0.11 mL) with stirring at 0° C. The reaction solution was stirred at room temperature for 2 hours, added water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The residue was filtered with hexane and obtained the title compound (225 mg) having the following physical properties.

Workup

  1. stirringThe reaction solution was stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. filtrationThe residue was filtered with hexane

Sources & evidence

ORD record
ord-fc01384fe3ad4af0acf70aad4196e27a
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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