Hydrochloric Acid → HCID 131736820, compound

HRID 1486843Notes

Reaction equation

HRID 1486843 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([O:20][C:21](=[O:45])[CH2:22][C@:23]1([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:36])[O:27][N:26]=[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)[CH2:24]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C.Cl>N1C=CC=CC=1.O>[CH2:13]([O:20][C:21](=[O:45])[CH2:22][C@:23]1([C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:36])[O:27][N:26]=[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:8](=[O:9])[C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)[CH:29]=2)[CH2:24]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 8857Ethyl Acetate2×HCID 131736821HCID 131736821, compound

Product 1

HCID 131736820HCID 131736820, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

4-Nitrobenzoyl chloride (105 g) was added in small portions to a solution of benzyl (5R)-5-(2-(benzyloxy)-2-oxoethyl)-3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (126 g) in pyridine (380 mL) at 20 C. The obtained mixture was stirred at room temperature for 1.5 hours. To the reaction mixture, ethyl acetate (650 mL) and 1 M hydrochloric acid (1300 mL) were added at 0 C, and then, ethyl acetate (1300 mL) and water (260 mL) were added. The organic layer was separated, and the aqueous layer was subjected to extraction with ethyl acetate (1300 mL). Combined organic layers were washed with diluted aqueous ammonia ((28% aqueous ammonia (26 mL)/water (1300 mL))×2), 1 M hydrochloric acid (1300 mL×2), and brine (1300 mL) and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was washed with diisopropyl ether (1500 mL) to obtain the title compound (165 g).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was subjected to extraction with ethyl acetate (1300 mL)
  3. washCombined organic layers were washed with diluted aqueous ammonia ((28% aqueous ammonia (26 mL)/water (1300 mL))×2), 1 M hydrochloric acid (1300 mL×2), and brine (1300 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washThe residue was washed with diisopropyl ether (1500 mL)

Sources & evidence

ORD record
ord-09c739e154a3418aa77f7d5bb36bdc62
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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