tert-Butyl N,N-dipropan-2-ylcarbamimidate → HCID 178450678, compound

HRID 27143Notes

Reaction equation

HRID 27143 reaction equation
[NH2:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:21]([OH:23])=[O:22])=[C:6]([CH:9]([S:15][C:16]3[NH:20][N:19]=[N:18][N:17]=3)[CH2:10][CH2:11][C:12](=[O:14])[NH2:13])[CH2:7][S:8][C@H:3]12.[C:26](OC(=N)N(C(C)C)C(C)C)([CH3:29])([CH3:28])[CH3:27]>C(Cl)Cl>[C:26]([O:22][C:21]([C:5]1[N:4]2[C:24](=[O:25])[CH:2]([NH2:1])[C@H:3]2[S:8][CH2:7][C:6]=1[CH:9]([S:15][C:16]1[NH:17][N:18]=[N:19][N:20]=1)[CH2:10][CH2:11][C:12](=[O:14])[NH2:13])=[O:23])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 22010542tert-Butyl N,N-dipropan-2-ylcarbamimidateHCID 1785139097-Amino-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid

Product 1

HCID 178450678HCID 178450678, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 19.3 g. (0.05 mol.) of 7-amino-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid in 500 ml. of dry methylene chloride is added in one portion 30.0 g. (0.15 mol.) of O-t-butyldiisopropylpseudourea in 50 ml. of methylene chloride and the mixture is stirred at ambient temperature for 24 hours. The precipitate is removed by filtration and the filtrate is evaporated to give 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 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 is extracted with two 150 ml. portions of ethyl acetate. The combined extracts are dried (MgSO4), filtered and evaporated to dryness to give 7-amino-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid t-butyl ester.

Workup

  1. additionTo a suspension of 19.3 g
  2. customThe precipitate is removed by filtration
  3. customthe filtrate is evaporated
  4. customto give a residue which
  5. filtrationof benzene and filtered again
  6. extractionThe filtrate is extracted with three 100 ml
  7. additionthe pH is adjusted to 7.5 by addition of solid sodium bicarbonate
  8. customThe organic layer is separated
  9. extractionthe aqueous phase is extracted with two 150 ml
  10. dry with materialThe combined extracts are dried (MgSO4)
  11. filtrationfiltered
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-f11b8c37a12540549fe51ebc977465c0
Source dataset
uspto-grants-1980_09
Patent number
US04220644

Reaction notes

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