Ethyl Acetate → HCID 14324465, compound

HRID 1709791Notes

Reaction equation

HRID 1709791 reaction equation
[C:1]([C:5]1[O:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16](O)=[O:17])=[CH:12][C:11]=2[N+:19]([O-:21])=[O:20])[C:7](=[O:22])[C:6]=1[CH2:23][Cl:24])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.C(Cl)(=O)OCC.[CH2:37]([NH2:53])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>O.C(N(CC)CC)C>[C:1]([C:5]1[O:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:17])[NH:53][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[CH:12][C:11]=2[N+:19]([O-:21])=[O:20])[C:7](=[O:22])[C:6]=1[CH2:23][Cl:24])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 8926HexadecylamineHCID 10928Ethyl chloroformateHCID 14324458HCID 14324458, compound

Product 1

HCID 14324465HCID 14324465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-15 °C

Procedure

81.6 g of 5-t-butyl-4-chloromethyl-2-(4-carboxy-2-nitrophenyl)-4-isoxazolin-3-one and 480 ml of ethyl acetate were mixed with each other, then cooled to -15° C. To this suspension was dropwise added 32.6 ml of triethylamine. Then, 22.0 ml of ethyl chlorocarbonate was dropwise added thereto while keeping the temperature of the mixture at not higher than -10° C. After reacting under such conditions for 50 minutes, 49 g of hexadecylamine was added thereto. After reacting for 10 minutes at -10° C., the temperature of the reaction mixture was gradually raised to room temperature, and the mixture was left overnight. Then, 400 ml of water was added thereto, and the organic layer was separated and concentrated using an evaporator to dryness. The residue was crystallized from methanol.

Workup

  1. customhigher than -10° C
  2. waitAfter reacting for 10 minutes at -10° C.
  3. temperaturethe temperature of the reaction mixture was gradually raised to room temperature
  4. waitthe mixture was left overnight
  5. customthe organic layer was separated
  6. concentrationconcentrated
  7. customan evaporator to dryness
  8. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-5e51284d172e4b19b910fb0bd9f452fe
Source dataset
uspto-grants-1990_08
Patent number
US04950764

Reaction notes

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