Pyridine → HCID 86756878, compound

HRID 1979191Notes

Reaction equation

HRID 1979191 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].N1C=CC=CC=1.[CH:40]1[C:52]2[CH:51]([CH2:53][O:54][C:55]([NH:57][C:58]3([C:63](O)=[O:64])[CH2:62][CH2:61][CH2:60][CH2:59]3)=[O:56])[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:44]=2[CH:43]=[CH:42][CH:41]=1>ClCCl.C(OCC)(=O)C>[CH:40]1[C:52]2[CH:51]([CH2:53][O:54][C:55]([NH:57][C:58]3([C:63]([N:25]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH:24][C:22](=[O:23])[C@@H:21]([C@@H:11]([C:9](=[O:10])[NH:8][O:7][CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)[CH2:12]/[CH:13]=[CH:14]/[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:64])[CH2:59][CH2:60][CH2:61][CH2:62]3)=[O:56])[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:44]=2[CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 978345Fmoc-cycloleucineHCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86756878HCID 86756878, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 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 3 ml of dichloromethane was treated under nitrogen at room temperature with 0.119 g of pyridine and a solution of the acid chloride prepared from 0.42 g of N-(9-fluorenylmethyloxycarbonyl)-cycloleucine in 3 ml of dichloromethane. The mixture was stirred at room temperature for 16 hours and diluted with ethyl acetate. The solution was washed with 5% aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution and then dried over anhydrous magnesium sulphate. The solvent was evaporated to give a foam, which was crystallized from diethyl ether/hexane to give 0.71 g of (E)-2′-[(1-(9-fluorenylmethyloxycarbonylamino)-1-cyclopentyl)carbonyl]-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoy]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide as a white solid.

Workup

  1. washThe solution was washed with 5% aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customThe solvent was evaporated
  4. customto give a foam, which
  5. customwas crystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-1f5c661f698d46649b2ea7039a054450
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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