(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methyl-2'-(2-ureidoacetyl)valerohydrazide → (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2'-isobutyl-4-methyl-2'-(2-ureidoacetyl)valerohydrazide

HRID 1979196Notes

Reaction equation

HRID 1979196 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:22]([NH:24][N:25]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:26](=[O:32])[CH2:27][NH:28][C:29]([NH2:31])=[O:30])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]>Cl.O1CCOCC1.C(OCC)C>[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:22]([NH:24][N:25]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:26](=[O:32])[CH2:27][NH:28][C:29]([NH2:31])=[O:30])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Participants

5

Reactant 1

HCID 86756885(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methyl-2'-(2-ureidoacetyl)valerohydrazide

Product 1

HCID 86756884(E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2'-isobutyl-4-methyl-2'-(2-ureidoacetyl)valerohydrazideYield 83.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.51 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(2-ureidoacetyl)valerohydrazide dissolved 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 0.36 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(2-ureidoacetyl)valerohydrazide 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-384a24952f444a13983b8f820b66bae7
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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