Dicyclohexylcarbodiimide → HCID 141557382, compound

HRID 1032197Notes

Reaction equation

HRID 1032197 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:51]([O:53][CH:54]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:52])[C:33]3[CH:38]=[C:37]([O:39][C:40](=[O:42])[CH3:41])[C:36]([O:43][C:44](=[O:46])[CH3:45])=[C:35]([O:47][C:48](=[O:50])[CH3:49])[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:67]1([CH:73]([O:80][C:81]([C:83]2[N:84]3[C@H:87]([S:88][CH2:89][C:90]=2[CH2:91][S:92][C:93]2[N:98]4[N:99]=[C:100]([C:102]([O:104][CH:105]([C:112]5[CH:117]=[CH:116][CH:115]=[CH:114][CH:113]=5)[C:106]5[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=5)=[O:103])[N:101]=[C:97]4[N:96]=[C:95]([CH3:118])[CH:94]=2)[C@H:86]([NH2:119])[C:85]3=[O:120])=[O:82])[C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:67]1([CH:73]([O:80][C:81]([C:83]2[N:84]3[C@H:87]([S:88][CH2:89][C:90]=2[CH2:91][S:92][C:93]2[N:98]4[N:99]=[C:100]([C:102]([O:104][CH:105]([C:112]5[CH:113]=[CH:114][CH:115]=[CH:116][CH:117]=5)[C:106]5[CH:107]=[CH:108][CH:109]=[CH:110][CH:111]=5)=[O:103])[N:101]=[C:97]4[N:96]=[C:95]([CH3:118])[CH:94]=2)[C@H:86]([NH:119][C:27](=[O:28])/[C:26](/[C:24]2[N:25]=[C:21]([NH:20][C:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=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:51]([O:53][CH:54]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:52])[C:33]2[CH:38]=[C:37]([O:39][C:40](=[O:42])[CH3:41])[C:36]([O:43][C:44](=[O:46])[CH3:45])=[C:35]([O:47][C:48](=[O:50])[CH3:49])[CH:34]=2)[C:85]3=[O:120])=[O:82])[C:74]2[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=2)[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13821813HCID 13821813, compoundHCID 14479215(2Z)-2-[2-benzhydryloxy-2-oxo-1-(3,4,5-triacetyloxyphenyl)ethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid

Product 1

HCID 141557382HCID 141557382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution containing the product obtained in Step 4 (2.2 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 (1.84 g) in dichloromethane (65 ml) was added dicyclohexylcarbodiimide (0.59 g), and the mixture was stirred overnight at room temperature. The insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the insoluble matters were removed by filtration. 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 0.86 g (less polar form) and 0.94 g (more polar form) of the objective compound.

Workup

  1. filtrationThe insoluble matters were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customthe insoluble matters were removed by filtration
  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 0.86 g (less polar form) and 0.94 g (more polar form) of the objective compound

Sources & evidence

ORD record
ord-2d5c348578bb4df2b8ad43a2663ca797
Source dataset
uspto-grants-1990_09
Patent number
US04956474

Reaction notes

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