Diisopropyl Ether → (R)-18-(2-(4-nitrophenoxy)-2-oxoethoxy)-18-oxooctadecan-7-yl 4-nitrobenzoate

HRID 522194Notes

Reaction equation

HRID 522194 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:21][C:22](=[O:32])[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([OH:3])=[O:2].[N+:33]([C:36]1[CH:41]=[CH:40][C:39]([O:42][C:43](=[O:46])[CH2:44]Br)=[CH:38][CH:37]=1)([O-:35])=[O:34].C(OC(C)C)(C)C>CC(C)=O.C(N(CC)CC)C>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([C:22]([O:21][C@@H:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:1]([O:3][CH2:44][C:43]([O:42][C:39]2[CH:38]=[CH:37][C:36]([N+:33]([O-:35])=[O:34])=[CH:41][CH:40]=2)=[O:46])=[O:2])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:32])=[CH:24][CH:25]=1)([O-:31])=[O:30]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 100667Acetic acid, 2-bromo-, 4-nitrophenyl esterHCID 1183658614-Nitro-benzoic acid 11-carboxy-1-hexyl-undecyl ester

Product 1

HCID 118365849(R)-18-(2-(4-nitrophenoxy)-2-oxoethoxy)-18-oxooctadecan-7-yl 4-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-Nitro-benzoic acid 11-carboxy-1-hexyl-undecyl ester (500 g) in dry Acetone, triethylamine (232 mL) at 10-15° C. was added Bromoacetic acid 4-nitro-phenyl ester (347 g). The solution was stirred at room temperature for 8 hours. 75% of the solvent was distilled off and cooled to room temperature. The resulting solid was poured onto cold water and pH was adjusted to 4-5 with dilute HCl. The resulting solid was filtered off and washed with chilled water (100 mL). The slurry was prepared with 1 lit Di Isopropyl Ether and filtered off. The resulting solid was then dried in vacuum oven at 60-80° C. to yield pure (R)-18-(2-(4-nitrophenoxy)-2-oxoethoxy)-18-oxooctadecan-7-yl 4-nitrobenzoate product as off white powder with a melting point of 130-133° C. The resulting compound was characterized by 1H NMR (CDCl3) δ 0.86 (t, 3H, CH3), 1.2-1.5 (m, 28H, 14×CH2), 1.68 (m, 2H, CH2), 2.42 (t, 2H, COCH2), 3.52 (m, 1H, CH), 5.2 (s, 2H, CH2) 7.42 (m, 2H, Ar) 8.4-8.52 (m, 6H, Ar).

Workup

  1. distillation75% of the solvent was distilled off
  2. temperaturecooled to room temperature
  3. additionThe resulting solid was poured onto cold water and pH
  4. filtrationThe resulting solid was filtered off
  5. washwashed with chilled water (100 mL)
  6. customThe slurry was prepared with 1
  7. filtrationfiltered off
  8. customThe resulting solid was then dried in vacuum oven at 60-80° C.

Sources & evidence

ORD record
ord-d68a17ba8925469585a6ac7f31a5e466
Source dataset
uspto-grants-2016_05
Patent number
US09328192B2

Reaction notes

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