tert-Butyl N,N-dipropan-2-ylcarbamimidate → HCID 178468125, compound

HRID 2057547Notes

Reaction equation

HRID 2057547 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]([C:9]([CH2:19][PH:20]([OH:22])=[O:21])([S:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:10][CH2:11][CH3:12])[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:6]([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[C:9]([CH2:19][PH:20]([O:22][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:21])([S:13][C:14]1[NH:18][N:17]=[N:16][N:15]=1)[O:10][CH2:11][CH3:12])=[O:25])([CH3:9])([CH3:7])[CH3:5]

Participants

4

Reactant 2

HCID 22010542tert-Butyl N,N-dipropan-2-ylcarbamimidateHCID 178468132HCID 178468132, compound

Product 1

HCID 178468125HCID 178468125, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 21.8 g (0.05 mol) of 7β-amino-3-(1-ethoxyhydroxyphosphinylmethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid in 500 ml of methylene chloride is added over a 30 minute interval a solution of 60.0 g (0.30 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 extracted with three 100 ml portions of cold 1 N 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 7β-amino-3-(1-ethoxy-t-butoxyphosphinylmethyltetrazol-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. extractionThe filtrate is extracted with three 100 ml portions of cold 1 N hydrochloric acid
  5. additionthe pH is adjusted to 7.5 by addition of solid sodium bicarbonate
  6. customThe organic layer is separated
  7. extractionthe aqueous phase is extracted with two 150 ml portions of ethyl acetate
  8. dry with materialThe combined extracts are dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-859cd9f907274e7fb048cd258117de7c
Source dataset
uspto-grants-1980_07
Patent number
US04211703

Reaction notes

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