Triethylamine → HCID 56981585, compound

HRID 744878Notes

Reaction equation

HRID 744878 reaction equation
[C:1]([S:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C@H:12]([C:28](O)=[O:29])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[N+:37]([C:40]1[CH:61]=[CH:60][C:43]([CH2:44][O:45][C:46]([NH:48][CH2:49][CH2:50][CH2:51][C:52]([N:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)=[O:53])=[O:47])=[CH:42][CH:41]=1)([O-:39])=[O:38].C(N(CC)CC)C>ClCCl.CN(C)C=O.C(Cl)(Cl)Cl>[C:1]([S:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[C@H:12]([C:28]([N:57]2[CH2:56][CH2:55][N:54]([C:52](=[O:53])[CH2:51][CH2:50][CH2:49][NH:48][C:46]([O:45][CH2:44][C:43]3[CH:42]=[CH:41][C:40]([N+:37]([O-:39])=[O:38])=[CH:61][CH:60]=3)=[O:47])[CH2:59][CH2:58]2)=[O:29])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19422427HCID 19422427, compoundHCID 57165102HCID 57165102, compound

Product 1

HCID 56981585HCID 56981585, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A 0.86 g portion of (2S,4S)-4-benzoylthio-1-(p-nitrobenzyloxycarbonyl)proline was suspended in 10 ml of dichloromethane, and 0.51 g of oxalyl chloride and one drop of dimethylformamide were added to the suspension, followed by 1 hour of reaction at room temperature. With cooling on an ice bath, to the solution were added 0.74 g of 1-(4-(p-nitrobenzyloxycarbonyl)aminobutyryl)piperazine and 0.41 g of triethylamine, followed by 3 hours of reaction at room temperature. The resulting reaction mixture was mixed with chloroform, washed with sodium bicarbonate aqueous solution, citric acid aqueous solution and sodium chloride aqueous solution in that order and then dried over sodium sulfate, followed by evaporation of the solvent under a reduced pressure. Thereafter, a residue was subjected to a silica gel column chromatography to yield 1.64 g of foamy (2S,4S)-4-benzoylthio -1-(p-nitrobenzyloxycarbonyl)-2-((1-(4-(p-nitrobenzyloxycarbonyl) aminobutyryl)piperazine-4-yl)carbonyl)pyrrolidine.

Workup

  1. customfollowed by 1 hour of reaction at room temperature
  2. temperatureWith cooling on an ice bath, to the solution
  3. customfollowed by 3 hours of reaction at room temperature
  4. customThe resulting reaction mixture
  5. washwashed with sodium bicarbonate aqueous solution, citric acid aqueous solution and sodium chloride aqueous solution in that order
  6. dry with materialdried over sodium sulfate
  7. customfollowed by evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-87347e38006d406da6346d09a349340f
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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