Pyridine → HCID 86757181, compound

HRID 1386562Notes

Reaction equation

HRID 1386562 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].C1(=O)N(CCS(Cl)(=O)=O)C(=O)C2=CC=CC=C12.N1C=CC=CC=1.[O:57]=[C:58]([S:72](Cl)(=[O:74])=[O:73])[CH2:59][N:60]1[C:64](=[O:65])[CH:63]2[C:66](=[O:70])[CH:67]=[CH:68][CH:69]=[C:62]2[C:61]1=[O:71]>ClCCl>[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][N:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[S:72]([C:58](=[O:57])[CH2:59][N:60]1[C:64](=[O:65])[CH:63]2[C:66](=[O:70])[CH:67]=[CH:68][CH:69]=[C:62]2[C:61]1=[O:71])(=[O:73])=[O:74])=[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

6

Reactant 4

HCID 1049PyridineHCID 3087392-Phthalimidoethanesulfonyl chlorideHCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazideHCID 867571821,3-Dioxo-2-phthalimidoethanesulphonyl chloride

Product 1

HCID 86757181HCID 86757181, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 8 ml of dichloromethane was treated with 0.287 g of 2-phthalimidoethanesulphonyl chloride and 0.1 ml of pyridine at room temperature under a nitrogen atmosphere. The mixture was stirred for 2 hours at room temperature and a further 0.287 g of 1,3-dioxo-2-phthalimidoethanesulphonyl chloride was added. The mixture was stirred overnight at room temperature and evaporated. The residue was dissolved in ethyl acetate and washed in sequence with water, 5% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. Drying over anhydrous magnesium sulphate and evaporation gave a residue which was triturated with diethyl ether to give 0.47 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-2′-(1,3-dioxo-2-phthalimidoethanesulphonyl)-4-methylvalerohydrazide in the form of a pale yellow solid.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed in sequence with water, 5% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  5. dry with materialDrying over anhydrous magnesium sulphate and evaporation
  6. customgave a residue which
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-fd3489cfba534be38def2788cfd296ff
Source dataset
uspto-grants-2001_07
Patent number
US06265446B1

Reaction notes

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