Dicyclohexylcarbodiimide → benzotriazol-1-yl (2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate

HRID 483024

Reaction equation

HRID 483024 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH3:32])/[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.O[N:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[N:35]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH3:32])/[C:27]([O:29][N:34]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[N:36]=[N:35]2)=[O:28])[N:25]=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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5928144(Z)-2-methoxymino-2-(2-(tritylamino)thiazol-4-yl)acetic acid

Product 1

HCID 88675991benzotriazol-1-yl (2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetic acid (2.22 g, 5 mmol) and 1-hydroxybenzotriazole (0.74 g, 5.5 mmol) in tetrahydrofuran (22 ml) was added N,N'-dicyclohexylcarbodiimide (1.14 g, 5.5 mmol) at 5°-10° C. and the mixture was stirred at the same temperature for 3 hours. Precipitated N,N'-dicyclohexylurea was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform (20 ml) and insoluble material was removed by filtration. The chloroform was evaporated and the residue was treated with a small quantity of ether to give colorless needles of 1-benzotriazolyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetate (2.60 g, 93%), mp 178°-179° C. (decomposition).

Workup

  1. customPrecipitated N,N'-dicyclohexylurea was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform (20 ml)
  4. custominsoluble material was removed by filtration
  5. customThe chloroform was evaporated
  6. additionthe residue was treated with a small quantity of ether

Sources & evidence

ORD record
ord-de584faa82294b62aa037648a02c0640
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Linked notes

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