Dicyclohexylcarbodiimide → HCID 16166018, compound

HRID 1032192Notes

Reaction equation

HRID 1032192 reaction equation
[C:1]1([C:7]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH:32]([C:47]([O:49][CH:50]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[O:48])[C:33]3[CH:38]=[CH:37][C:36]([O:39][C:40](=[O:42])[CH3:41])=[C:35]([O:43][C:44](=[O:46])[CH3:45])[CH:34]=3)/[C:27](O)=[O:28])[N:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:63]1([CH:69]([O:76][C:77]([C:79]2[N:80]3[C@H:83]([S:84][CH2:85][C:86]=2[CH2:87][S:88][C:89]2[N:94]4[N:95]=[C:96]([C:98]([O:100][CH:101]([C:108]5[CH:113]=[CH:112][CH:111]=[CH:110][CH:109]=5)[C:102]5[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=5)=[O:99])[N:97]=[C:93]4[N:92]=[C:91]([CH3:114])[CH:90]=2)[C@H:82]([NH2:115])[C:81]3=[O:116])=[O:78])[C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:63]1([CH:69]([O:76][C:77]([C:79]2[N:80]3[C@H:83]([S:84][CH2:85][C:86]=2[CH2:87][S:88][C:89]2[N:94]4[N:95]=[C:96]([C:98]([O:100][CH:101]([C:108]5[CH:109]=[CH:110][CH:111]=[CH:112][CH:113]=5)[C:102]5[CH:103]=[CH:104][CH:105]=[CH:106][CH:107]=5)=[O:99])[N:97]=[C:93]4[N:92]=[C:91]([CH3:114])[CH:90]=2)[C@H:82]([NH:115][C:27](=[O:28])/[C:26](/[C:24]2[N:25]=[C:21]([NH:20][C:7]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[S:22][CH:23]=2)=[N:30]\[O:31][CH:32]([C:47]([O:49][CH:50]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:48])[C:33]2[CH:38]=[CH:37][C:36]([O:39][C:40](=[O:42])[CH3:41])=[C:35]([O:43][C:44](=[O:46])[CH3:45])[CH:34]=2)[C:81]3=[O:116])=[O:78])[C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13821813HCID 13821813, compoundHCID 14050777HCID 14050777, compound

Product 1

HCID 16166018HCID 16166018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of the crude product obtained in Step 5 (5.6 g) and (6R,7R)-7-amino-3-[(2-diphenylmethyloxycarbonyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester (5.0 g) in dichloromethane (170 ml) was added dicyclohexylcarbodiimide (1.4 g), and the mixture was stirred at room temperature for five hours. After filtering off the insoluble matters, the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the insoluble matters were filtered off. The filtrate was washed with brine and dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, giving 0.73 g (less polar form) and 1.39 g (more polar form) of the objective compounds.

Workup

  1. filtrationAfter filtering off the insoluble matters
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationthe insoluble matters were filtered off
  5. washThe filtrate was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe dried solution was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. customgiving 0.73 g (less polar form) and 1.39 g (more polar form) of the objective compounds

Sources & evidence

ORD record
ord-3ef44d455375476c99232ea67437d929
Source dataset
uspto-grants-1990_09
Patent number
US04956474

Reaction notes

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