tert-Butyl N,N-dipropan-2-ylcarbamimidate → HCID 178450703, compound

HRID 1390898Notes

Reaction equation

HRID 1390898 reaction equation
[NH2:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:22]([OH:24])=[O:23])=[C:6]([CH:9]([S:16][C:17]3[NH:21][N:20]=[N:19][N:18]=3)[CH2:10][CH2:11][S:12](=[O:15])(=[O:14])[NH2:13])[CH2:7][S:8][C@H:3]12.[C:27](OC(=N)N(C(C)C)C(C)C)([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:23][C:22]([C:5]1[N:4]2[C:25](=[O:26])[CH:2]([NH2:1])[C@H:3]2[S:8][CH2:7][C:6]=1[CH:9]([S:16][C:17]1[NH:18][N:19]=[N:20][N:21]=1)[CH2:10][CH2:11][S:12](=[O:14])(=[O:15])[NH2:13])=[O:24])([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 22010542tert-Butyl N,N-dipropan-2-ylcarbamimidateHCID 178508099HCID 178508099, compound

Product 1

HCID 178450703HCID 178450703, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 21.1 g. (0.05 mol.) of 7-amino3-[1-(2-sulfamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4carboxylic acid in 500 ml. of dry methylene chloride is added in one portion a solution of 30.0 g. (0.15 mol.) of O-t-butyldiisopropylpseudourea in 50 ml. of methylene chloride. The mixture is stirred at ambient temperature for 24 hours. The precipitate is removed by filtration and the filtrate evaporated to a residue which is taken up in 200 ml. of benzene and filtered again. The filtrate is extracted with three 100 ml. portions of cold 1N hydrochloric acid. The acidic aqueous extracts are layered with ethyl acetate and the pH adjusted to 7.5 with solid sodium bicarbonate. The organic layer is separated and the aqueous phase is extracted with two 150 ml. portions of ethyl acetate. The combined extracts are dried (MgSO4), filtered and evaporated to give 7-amino-3-[1-(2-sulfamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid t-butyl ester.

Workup

  1. additionTo a suspension of 21.1 g
  2. customThe precipitate is removed by filtration
  3. customthe filtrate evaporated to a residue which
  4. filtrationof benzene and filtered again
  5. extractionThe filtrate is extracted with three 100 ml
  6. customThe organic layer is separated
  7. extractionthe aqueous phase is extracted with two 150 ml
  8. dry with materialThe combined extracts are dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-7942cf3ffe094161920b0b9b1ff6f119
Source dataset
uspto-grants-1979_02
Patent number
US04140694

Reaction notes

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