Hydrochloric Acid → (E)-2'-(beta-alanyl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide hydrochloride

HRID 1979193Notes

Reaction equation

HRID 1979193 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]([N:13]([CH2:42][CH:43]([CH3:45])[CH3:44])[NH:14][C:15](=[O:41])[C@@H:16]([C@@H:21]([C:31](=[O:40])[NH:32][O:33]C1CCCCO1)[CH2:22]/[CH:23]=[CH:24]/[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:12])=O)(C)(C)C.[ClH:46]>O1CCOCC1.C(OCC)C>[ClH:46].[NH2:8][CH2:9][CH2:10][C:11]([N:13]([CH2:42][CH:43]([CH3:45])[CH3:44])[NH:14][C:15](=[O:41])[C@@H:16]([C@@H:21]([C:31](=[O:40])[NH:32][OH:33])[CH2:22]/[CH:23]=[CH:24]/[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86756882(E)-2'-(N-tert.-butoxycarbonyl-beta-alanyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86756880(E)-2'-(beta-alanyl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.47 g of (E)-2′-(N-tert.-butoxycarbonyl-β-alanyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 5 ml of 4M hydrogen chloride in dioxan was stirred for 2 hours at room temperature and diluted with diethyl ether. The solid was filtered off, washed with diethyl ether and dried to give 0.29 g of (E)-2′-(β-alanyl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide hydrochloride in the form of a white solid.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-c65cab3ae34b436a99625dbd62301f13
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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