N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → (E)-2'-(N-tert.-butoxycarbonyl-beta-alanyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

HRID 1979194Notes

Reaction equation

HRID 1979194 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([NH:24][NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].[C:34]([O:38][C:39]([NH:41][CH2:42][CH2:43][C:44](O)=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[C:34]([O:38][C:39]([NH:41][CH2:42][CH2:43][C:44]([N:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[NH:24][C:22](=[O:23])[C@@H:21]([C@@H:11]([C:9](=[O:10])[NH:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 3

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86756882(E)-2'-(N-tert.-butoxycarbonyl-beta-alanyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazideYield 76.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.459 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 5 ml of dimethylformamide was cooled to 0° C. and treated with 0.378 g of N-tert.-butoxycarbonyl-β-alanine and 0.383 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodimide hydrochloride. The mixture was stirred at room temperature for 16 hours and diluted with ethyl acetate. The solution was washed in succession with water, 5% citric acid solution and water, dried over anhydrous magnesium sulphate and evaporated. Chromatography on silica gel using ethyl acetate/hexane (1:1) for the elution followed by evaporation gave 0.48 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 the form of a white foam.

Workup

  1. washThe solution was washed in succession with water, 5% citric acid solution and water
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customevaporated
  4. washfor the elution
  5. customfollowed by evaporation

Sources & evidence

ORD record
ord-45a1710c3fdb45d79e9905cb77c5d73f
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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