Dicyclohexylcarbodiimide → HCID 16170836, compound

HRID 1032198Notes

Reaction equation

HRID 1032198 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][O:88][C:89](=[O:91])[CH3:90])[C@H:82]([NH2:92])[C:81]3=[O:93])=[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][O:88][C:89](=[O:91])[CH3:90])[C@H:82]([NH:92][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:93])=[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 10575011HCID 10575011, compoundHCID 14050777HCID 14050777, compound

Product 1

HCID 16170836HCID 16170836, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution containing the product obtained in Step 5 of Example 8 (3.0 g) and (6R,7R)-7-amino-3-acetoxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester (1.58 g) in dichloromethane (90 ml) was added dicyclohexylcarbodiimide (0.74 g), and the mixture was stirred at room temperature for 4 hours. Insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was redissolved in ethyl acetate and the insoluble matters were removed by filtration. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, giving 2.42 g of the objective compound.

Workup

  1. filtrationInsoluble matters were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was redissolved in ethyl acetate
  4. customthe insoluble matters were removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7396179d83f943d685251ddd848a93d6
Source dataset
uspto-grants-1990_09
Patent number
US04956474

Reaction notes

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