Dicyclohexylcarbodiimide → HCID 73708098, compound

HRID 1904138Notes

Reaction equation

HRID 1904138 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][CH2:33][N:34]=[N+:35]=[N-:36])[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:37][N:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[N:39]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][CH2:33][N:34]=[N+:35]=[N-:36])[C:27]([OH:29])=[O:28])[N:25]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1.[OH:37][N:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[N:39]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 53777913HCID 53777913, compound

Product 1

HCID 73708098HCID 73708098, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 9.84 g of the product of Step B, 2.93 g of 1-hydroxy-1H-benzotriazol, 4.88 g of dicyclohexylcarbodiimide and 130 ml of anhydrous methylene chloride was stirred for 20 hours at room temperature and was vacuum filtered to remove dicyclohexylurea. The filtrate was washed with aqueous sodium bicarbonate solution, then with water, was dried and evaporated to dryness under reduced pressure. The residue was taken up in ethyl acetate and after cooling the mixture at 0° C. for 30 minutes, the mixture was vacuum filtered to obtain 7.31 g of 1-hydroxy-1H-benzotriazole 2-(2-tritylamino-4-thiazolyl)-2-(2-azidoethoxyimino)-acetate. Another 1.5 g of the product were recovered by evaporation of the filtrate.

Workup

  1. filtrationfiltered
  2. customto remove dicyclohexylurea
  3. washThe filtrate was washed with aqueous sodium bicarbonate solution
  4. dry with materialwith water, was dried
  5. customevaporated to dryness under reduced pressure
  6. temperatureafter cooling the mixture at 0° C. for 30 minutes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-44a27cfc200a463db6fa2903d22db2b9
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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