Hydrochloric Acid → HCID 118292783, compound

HRID 1486907Notes

Reaction equation

HRID 1486907 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:66])[CH2:22][C:23]1([CH2:55][C:56](=[O:65])[O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[O:27][N:26]=[C:25]([C:28]2[CH:33]=[C:32]([OH:34])[CH:31]=[CH:30][C:29]=2[CH2:35][CH2:36][C:37]([N:39]2[CH2:44][CH2:43][CH:42]([C:45]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:46])[CH2:41][CH2:40]2)=[O:38])[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>[CH2:58]([O:57][C:56](=[O:65])[CH2:55][C:23]1([CH2:22][C:21](=[O:66])[O:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:27][N:26]=[C:25]([C:28]2[CH:33]=[C:32]([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:31]=[CH:30][C:29]=2[CH2:35][CH2:36][C:37]([N:39]2[CH2:44][CH2:43][CH:42]([C:45]([O:47][CH2:48][C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)=[O:46])[CH2:41][CH2:40]2)=[O:38])[CH2:24]1)[C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 8857Ethyl AcetateHCID 118292734HCID 118292734, compound

Product 1

HCID 118292783HCID 118292783, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Nitrobenzoyl chloride (405 mg) was added in small portions to a solution of benzyl 1-(3-(2-(5,5-bis(2-(benzyloxy)-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoyl)piperidine-4-carboxylate (800 mg) in pyridine (4 mL) at 0 C. The obtained mixture was stirred at room temperature for 45 minutes. To the reaction mixture, ethyl acetate and 1 M hydrochloric acid were added 0 C, followed by extraction with ethyl acetate. Combined organic layers were washed with diluted aqueous ammonia ((28% aqueous ammonia (0.5 mL)/water (25 mL))×2), 1 M hydrochloric acid, and brine and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure to obtain the title compound (939 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washCombined organic layers were washed with diluted aqueous ammonia ((28% aqueous ammonia (0.5 mL)/water (25 mL))×2), 1 M hydrochloric acid, and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1b06a20b389e4e73896611da2da1bfc4
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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