Dicyclohexylcarbodiimide → HCID 54349452, compound

HRID 1649267Notes

Reaction equation

HRID 1649267 reaction equation
[C:1]([O:5][C:6]([C:8]1([O:12][N:13]=[C:14]([C:18]2[N:19]=[C:20]([NH:23][C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[S:21][CH:22]=2)[C:15]([OH:17])=O)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:43][CH:44]1[C:51](=[O:52])[N:50]2[CH:45]1[S:46](=[O:82])[CH2:47][C:48]([CH:69]=[CH:70][O:71][S:72]([C:75]1[CH:81]=[CH:80][C:78]([CH3:79])=[CH:77][CH:76]=1)(=[O:74])=[O:73])=[C:49]2[C:53]([O:55][CH:56]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:54].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:56]([O:55][C:53]([C:49]1[N:50]2[CH:45]([S:46](=[O:82])[CH2:47][C:48]=1[CH:69]=[CH:70][O:71][S:72]([C:75]1[CH:76]=[CH:77][C:78]([CH3:79])=[CH:80][CH:81]=1)(=[O:73])=[O:74])[CH:44]([NH:43][C:15](=[O:17])[C:14](=[N:13][O:12][C:8]1([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11][CH2:10][CH2:9]1)[C:18]1[N:19]=[C:20]([NH:23][C:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[S:21][CH:22]=1)[C:51]2=[O:52])=[O:54])([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 539396637-Amino-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide2×HCID 54272804HCID 54272804, compound

Product 1

HCID 54349452HCID 54349452, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

The syn isomer of 2-(1-t-butoxycarbonylcyclobutoxyimino)-2-(2-tritylaminothiazol-4-yl)-acetic acid prepared according to Belgian Patent 876,541 (4.42 g) and 4-dimethylaminopyridine (0.25 g) are added to a solution of the E form of 7-amino-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (product 7d) (4.34 g) in methylene chloride (50 cc). The mixture is cooled to 5° C. and a solution of N,N'-dicyclohexylcarbodiimide (1.69 g) in methylene chloride (30 cc) is added dropwise in the course of 10 minutes. The temperature is left to rise, the mixture is stirred for 4 hours at 20° C. and concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa) and the residue is taken up in ethyl acetate (200 cc). The solution is washed with water (2×100 cc), 0.1 N hydrochloric acid (100 cc), a saturated aqueous solution of sodium bicarbonate (100 cc) and water (100 cc), dried over sodium sulphate and filtered and the filtrate is concentrated to dryness at 25° C. under 20 mm Hg (2.7 kPa). The residue is chromatographed on a column of Merck silica gel (0.06-0.2) (180 g) (diameter of the column: 3 cm, height: 60 cm). Elution is carried out with a 70/30 (by volume) cyclohexane/ethyl acetate mixture (1 liter), 60 cc fractions being collected. Fractions 6 to 10 are concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa) and this yields a product (7a) (2.7 g) in the form of a cream-coloured powder.

Workup

  1. waitThe temperature is left
  2. concentrationconcentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)
  3. washThe solution is washed with water (2×100 cc), 0.1 N hydrochloric acid (100 cc)
  4. dry with materiala saturated aqueous solution of sodium bicarbonate (100 cc) and water (100 cc), dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness at 25° C. under 20 mm Hg (2.7 kPa)
  7. customThe residue is chromatographed on a column of Merck silica gel (0.06-0.2) (180 g) (diameter of the column
  8. washElution
  9. custombeing collected
  10. concentrationFractions 6 to 10 are concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)

Sources & evidence

ORD record
ord-d31642104a1b4e7693acf6c9e81deeb3
Source dataset
uspto-grants-1983_11
Patent number
US04415562

Reaction notes

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