Ethyl Acetate → HCID 14324465, compound

HRID 1460948Notes

Reaction equation

HRID 1460948 reaction equation
C(OCC)(=O)C.[C:7]([C:11]1[O:15][N:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][C:17]=2[N+:25]([O-:27])=[O:26])[C:13](=[O:28])[C:12]=1[CH2:29][Cl:30])([CH3:10])([CH3:9])[CH3:8].C(OC(Cl)=O)C.[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:7]([C:11]1[O:15][N:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:23])[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:18][C:17]=2[N+:25]([O-:27])=[O:26])[C:13](=[O:28])[C:12]=1[CH2:29][Cl:30])([CH3:9])([CH3:10])[CH3:8]

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

Ethyl acetate (480 ml) was mixed with 81.6 grams of 5-t-butyl-4-chloromethyl-2-(4-carboxy-2-nitrophenyl)-4-iso-oxazolin-3-one and the mixture was cooled to -15° C. Triethylamine (32.6 ml) was added dropwise to this suspension and then 22.0 ml of ethylchlorocarbonate was added dropwise while maintaining the temperature below -10° C. Hexadecylamine (49 grams) was added after reacting for a further period of 50 minutes. After reacting the mixture at -10° C. for a period of 10 minutes the temperature was gradually raised to room temperature and the mixture was left to stand overnight. Next 400 ml of water was added, the mixture was separated and the organic layer was recovered and concentrated to dryness. The residue was recrystallized from methanol.

Workup

  1. temperaturewhile maintaining the temperature below -10° C
  2. customat -10° C.
  3. customof 10 minutes
  4. temperaturewas gradually raised to room temperature
  5. waitthe mixture was left
  6. waitto stand overnight
  7. customthe mixture was separated
  8. customthe organic layer was recovered
  9. concentrationconcentrated to dryness
  10. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-401f8e3488b54c0b82489401f81f5fa3
Source dataset
uspto-grants-1991_12
Patent number
US05073473

Reaction notes

Loading…