Triethylamine → 950483-64-4

HRID 1173767Notes

Reaction equation

HRID 1173767 reaction equation
[CH2:1]([C@H:4]1[O:6][C@@H:5]1[C:7]([OH:9])=O)[CH2:2][CH3:3].C(N(CC)CC)C.C(OC(Cl)=O)C.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>O1CCCC1>[CH:23]1([NH:26][C:7]([C@@H:5]2[C@@H:4]([CH2:1][CH2:2][CH3:3])[O:6]2)=[O:9])[CH2:25][CH2:24]1

Participants

6

Conditions

Temperature
-20 °C

Procedure

(2S,3R)-3-Propyl-2-oxiranecarboxylic acid (118 mg, 0.8 mmol), triethylamine (0.8 mmol) and tetrahydrofuran (2 ml) were mixed, and the mixture was cooled to −20° C. A tetrahydrofuran solution (1 ml) of ethoxycarbonyl chloride (86 mg, 0.8 mmol) was gradually added, and the mixture was stirred at the same temperature for 30 minutes. A tetrahydrofuran solution (1 ml) of cyclopropylamine (48 mg, 0.8 mmol) was gradually added dropwise, and the mixture was stirred at the same temperature for 2 hours and at room temperature for 2 hours. After the reaction was quenched with water (10 ml), ethyl acetate (10 ml) was added and the solvent was evaporated away under reduced pressure. The mixture was extracted with ethyl acetate (10 ml), and washed with water (5 ml). The solvent was evaporated away under reduced pressure to obtain the title compound as a colorless oil (0.10 g, yield: 76%).

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hours and at room temperature for 2 hours
  2. customAfter the reaction was quenched with water (10 ml), ethyl acetate (10 ml)
  3. additionwas added
  4. customthe solvent was evaporated away under reduced pressure
  5. extractionThe mixture was extracted with ethyl acetate (10 ml)
  6. washwashed with water (5 ml)
  7. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-626224b7b73f4b84b19d888ca068bd7c
Source dataset
uspto-grants-2010_11
Patent number
US07834190B2

Reaction notes

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