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Isobutyl chloroformate → HCID 178477369, compound

HRID 224907
Notes
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Reaction equation

HRID 224907 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:14][C:13]([CH2:15][C:16]([OH:18])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(Cl)=O)C(C)C.[C:27]1([CH:33]([O:40][C:41]([C:43]2[N:48]3[C:49](=[O:52])[C@@H:50]([NH2:51])[C@H:47]3[S:46][CH2:45][C:44]=2[CH:53]([S:55][C:56]2[NH:60][N:59]=[N:58][N:57]=2)[CH3:54])=[O:42])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl.CN1CCOCC1>[C:27]1([CH:33]([O:40][C:41]([C:43]2[N:48]3[C:49](=[O:52])[C@@H:50]([NH:51][C:16](=[O:18])[CH2:15][C:13]4[S:14][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:11][CH:12]=4)[C@H:47]3[S:46][CH2:45][C:44]=2[CH:53]([S:55][C:56]2[NH:60][N:59]=[N:58][N:57]=2)[CH3:54])=[O:42])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62365Isobutyl chloroformateHCID 202932812-[5-({[(Tert-butoxy)carbonyl]amino}methyl)thiophen-2-yl]aceticacidHCID 178477368HCID 178477368, compound

Product 1

HCID 178477369HCID 178477369, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×
HCID 79724-MethylmorpholineSolvent

Conditions

Temperature
-20 °C

Procedure

5.43 g of 2-(5-tert.-butoxycarbonylaminomethyl-2-thienyl)-acetic acid are dissolved in 200 ml of methylene chloride containing 2.20 ml of 4-methyl-morpholine, the solution, from which moisture is kept excluded, is cooled to -20° C. and 2.86 ml of chloroformic acid isobutyl ester are added dropwise. After 30 minutes, a solution of 9.35 g of 7β-amino-3-(1-methyl-5-tetrazolylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester in 100 ml of methylene chloride is added, after which stirring is continued for one hour at -20° C. and for 16 hours whilst slowly warming to room temperature. The mixture is poured out onto ice-cold water, the organic solution is separated off and the aqueous phase is again extracted with 100 ml of methylene chloride. The organic extracts are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. Crystallisation of the residue from a mixture of methyl acetate and diethyl ether gives 7β-[2-(5-tert.-butoxycarbonylaminomethyl-2-thienyl)-acetylamino]-3-(1-methyl-5-tetrazolylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester, thin layer chromatogram (silica gel): Rf= 0.38 (system: chloroform/ethyl acetate/acetic acid, 80:19:1); ultraviolet absorption spectrum (in 95% strength aqueous ethanol): shoulders at 242 mμ (ε=16,400) and 274 mμ (ε=9,200); infrared absorption spectrum (in mineral oil): characteristic bands at 3.03μ, 5.58μ, 5.79μ, 6.12μ and 6.51μ.

Workup

  1. waitis continued for one hour at -20° C. and for 16 hours
  2. temperaturewhilst slowly warming to room temperature
  3. additionThe mixture is poured out onto ice-cold water
  4. customthe organic solution is separated off
  5. extractionthe aqueous phase is again extracted with 100 ml of methylene chloride
  6. washThe organic extracts are washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated
  9. customCrystallisation of the residue
  10. additionfrom a mixture of methyl acetate and diethyl ether

Sources & evidence

ORD record
ord-183d416d11cb4b9b8cf349a7afd0e56b
Source dataset
uspto-grants-1980_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04234578

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes