tert-Butyl N,N-dipropan-2-ylcarbamimidate → HCID 178450690, compound

HRID 866883Notes

Reaction equation

HRID 866883 reaction equation
[NH2:1][C@@H:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([CH:9]([S:17][C:18]3[NH:22][N:21]=[N:20][N:19]=3)[CH2:10][CH2:11][NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:7][S:8][C@H:3]12.[C:28](OC(=N)N(C(C)C)C(C)C)([CH3:31])([CH3:30])[CH3:29]>C(Cl)Cl>[C:28]([O:24][C:23]([C:5]1[N:4]2[C:26](=[O:27])[C@@H:2]([NH2:1])[C@H:3]2[S:8][CH2:7][C:6]=1[CH:9]([S:17][C:18]1[NH:19][N:20]=[N:21][N:22]=1)[CH2:10][CH2:11][NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[O:25])([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 22010542tert-Butyl N,N-dipropan-2-ylcarbamimidateHCID 178505105HCID 178505105, compound

Product 1

HCID 178450690HCID 178450690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 21.8 g (0.05 mol) of 7β-amino-3-[1-(2-methanesulfonamidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid in 500 ml of methylene chloride is added over a 30 minute interval a solution of 30.0 g (0.15 mol) of O-t-butyldiisopropylpseudourea in 100 ml of methylene chloride. The mixture is stirred at ambient temperature for 72 hours. The precipitate is removed by filtration and the filtrate is evaporated to a residue which is taken up in 200 ml of benzene and filtered again. The filtrate is extraced with three 100 ml portions of cold 1N hydrochloric acid. The aqueous extracts are layered with ethyl acetate and the pH is adjusted to 7.5 by addition of solid sodium bicarbonate. The organic layer is separated and the aqueous phase extracted with two 150 ml portions of ethyl acetate. The combined extracts are dried (MgSO4), filtered and evaporated to dryness to give 7β-amino-3-[1-(2-methanesulfonamidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid t-butyl ester.

Workup

  1. customThe precipitate is removed by filtration
  2. customthe filtrate is evaporated to a residue which
  3. filtrationfiltered again
  4. additionthe pH is adjusted to 7.5 by addition of solid sodium bicarbonate
  5. customThe organic layer is separated
  6. extractionthe aqueous phase extracted with two 150 ml portions of ethyl acetate
  7. dry with materialThe combined extracts are dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-db393145565040a5a4ab9a657dbfa1cf
Source dataset
uspto-grants-1978_07
Patent number
US04101656

Reaction notes

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