Phosgene → (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-N-(2,5-dioxo 1-imidazolidinyl)valeramide

HRID 651780Notes

Reaction equation

HRID 651780 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:19]([NH:21][NH:22][C:23](=[O:26])[CH2:24][NH2:25])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1CC[O:36][CH2:35]C1)C.C(Cl)(Cl)=O>ClCCl.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:19]([NH:21][N:22]1[C:23](=[O:26])[CH2:24][NH:25][C:35]1=[O:36])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 6371PhosgeneHCID 7525EthylmorpholineHCID 86757290(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2'-glycinyl-4-methylvalerohydrazide

Product 1

HCID 69709364(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-N-(2,5-dioxo 1-imidazolidinyl)valeramide

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.83 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2′-glycinyl-4-methylvalerohydrazide in 50 ml of dichloromethane was cooled to 0° C. under nitrogen and treated with 0.76 ml of N-ethylmorpholine and 1.34 ml of a 1.93M solution of phosgene in toluene. The mixture was left to warm to room temperature and was stirred for 3 hours. The mixture was diluted with ethyl acetate and washed with 2M aqueous hydrogen chloride and saturated aqueous sodium chloride. The organic phase was dried over anhydrous magnesium sulphate and evaporated. Trituration of the residue with diethyl ether gave 0.783 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-N-(2,5-dioxo 1-imidazolidinyl)valeramide in the form of a white solid.

Workup

  1. waitThe mixture was left
  2. washwashed with 2M aqueous hydrogen chloride and saturated aqueous sodium chloride
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-3b61d47616484774a91a2b18f663d33a
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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