1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2'-isobutyl-2'-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide

HRID 1979205Notes

Reaction equation

HRID 1979205 reaction equation
C([C@H]([C@@H:14]([CH2:45][CH:46]([CH3:48])[CH3:47])[C:15]([NH:17][N:18]([CH2:41][CH:42]([CH3:44])[CH3:43])[C:19](=[O:40])[C@@H:20]([CH3:39])[NH:21][C:22]([O:24][CH2:25][CH:26]1[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])=[O:16])C/C=C/C1C=CC=CC=1)(O)=O.O1CCCCC1ON.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[CH2:41]([N:18]([C:19](=[O:40])[C@@H:20]([CH3:39])[NH:21][C:22]([O:24][CH2:25][CH:26]1[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])[NH:17][C:15](=[O:16])[CH2:14][CH2:45][CH:46]([CH3:48])[CH3:47])[CH:42]([CH3:43])[CH3:44]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 88071337(e)-2(r)-[1(s)-(Carboxy)-4-phenyl-3-butenyl]-2'-isobutyl-2'-[n-(9-fluorenylmethoxycarbonyl)-d-alanyl]-4-methylvalerohydrazide

Product 1

HCID 1317225872'-isobutyl-2'-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.85 g of (E)-2(R)-[1(S)-(carboxy)-4-phenyl-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethoxycarbonyl)-D-alanyl]-4-methylvalerohydrazide in 3 ml of dimethylformamide was treated with 0.60 g of O-(tetrahydro-2H-pyran-2(RS)-yl)hydroxylamine and 0.54 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. The mixture was stirred overnight at room temperature and then diluted with ethyl acetate and washed with 5% aqueous citric acid, 5% aqueous sodium hydrogen carbonate and brine. The ethyl acetate layer was then dried over magnesium sulphate and evaporated. The residue was triturated with hexaneldiethyl ether (2:1) to give 1.67 g of (E)-2(R)-[1(S)-(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethoxycarbonyl)-D-alanyl]-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. washwashed with 5% aqueous citric acid, 5% aqueous sodium hydrogen carbonate and brine
  2. dry with materialThe ethyl acetate layer was then dried over magnesium sulphate
  3. customevaporated
  4. customThe residue was triturated with hexaneldiethyl ether (2:1)

Sources & evidence

ORD record
ord-db4f2df8e6314883a31215668decdd56
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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