Triethylamine → HCID 136197341, compound

HRID 539881Notes

Reaction equation

HRID 539881 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[C:14]1[NH:15][C:16](=[O:24])[C:17]([CH2:22][CH3:23])=[C:18]([CH2:20][CH3:21])[N:19]=1)[CH2:2][CH3:3].S(Cl)(Cl)=O.[NH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(N(CC)CC)C>ClCCl>[CH2:20]([C:18]1[N:19]=[C:14]([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][C:5]=2[O:4][CH2:1][CH2:2][CH3:3])[C:9]([NH:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:10])[NH:15][C:16](=[O:24])[C:17]=1[CH2:22][CH3:23])[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12176Glycine ethyl esterHCID 24386Thionyl ChlorideHCID 136197410HCID 136197410, compound

Product 1

HCID 136197341HCID 136197341, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (250 mg, 0.76 mmol) of example 58 was suspended in dichloromethane (20 ml), and added with thionyl chloride (2 ml), followed by refluxing for 2 h to clear the reaction mixture. The reaction mixture was concentrated off thionyl chloride, and added with dichloromethane. Under ice-bath, the reaction mixture was added dropwise into a dichloromethane solution (20 ml) containing ethyl 2-aminoacetate (80 mg, 0.727 mmol) and triethylamine (0.2 ml, 1.454 mmol), followed by stirring for 0.5 h. The reaction mixture was then washed with water (20 ml) and saturated saline (20 ml) respectively. The organic layer was dried with anhydrous sodium sulfate, and concentrated. The residue was passed through a silica gel column to give the white title compound (100 mg, yield: 33%). 1H NMR (CDCl3) δ: 11.01 (1H, br), 8.87 (1H, d), 8.00 (1H, dd), 7.08 (1H, d), 6.87 (1H, br), 4.27 (2H, q), 4.25 (2H, t), 4.21 (2H, t), 2.69 (2H, q), 2.59 (2H, q), 2.00 (2H, m), 1.32 (3H, t), 1.30 (3H, t), 1.15 (6H, t).

Workup

  1. temperatureby refluxing for 2 h
  2. concentrationThe reaction mixture was concentrated off thionyl chloride
  3. additionadded with dichloromethane
  4. additionUnder ice-bath, the reaction mixture was added dropwise into a dichloromethane solution (20 ml)
  5. washThe reaction mixture was then washed with water (20 ml) and saturated saline (20 ml) respectively
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-648c8e02a0d34e789217c19464fe4b14
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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