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Dicyclohexylcarbodiimide → HCID 16170823, compound

HRID 1032190
Notes
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Reaction equation

HRID 1032190 reaction equation
[C:1]1([C:7]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][C:33]3[CH:38]=[C:37]([OH:39])[C:36]([O:40][C:41](=[O:43])[CH3:42])=[CH:35][C:34]=3[C:44]([O:46][CH:47]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:45])/[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:60]1([CH:66]([O:73][C:74]([C:76]2[N:77]3[C@H:80]([S:81][CH2:82][C:83]=2[CH2:84][S:85][C:86]2[N:91]4[N:92]=[C:93]([C:95]([O:97][CH:98]([C:105]5[CH:110]=[CH:109][CH:108]=[CH:107][CH:106]=5)[C:99]5[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=5)=[O:96])[N:94]=[C:90]4[N:89]=[C:88]([CH3:111])[CH:87]=2)[C@H:79]([NH2:112])[C:78]3=[O:113])=[O:75])[C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:60]1([CH:66]([O:73][C:74]([C:76]2[N:77]3[C@H:80]([S:81][CH2:82][C:83]=2[CH2:84][S:85][C:86]2[N:91]4[N:92]=[C:93]([C:95]([O:97][CH:98]([C:105]5[CH:106]=[CH:107][CH:108]=[CH:109][CH:110]=5)[C:99]5[CH:100]=[CH:101][CH:102]=[CH:103][CH:104]=5)=[O:96])[N:94]=[C:90]4[N:89]=[C:88]([CH3:111])[CH:87]=2)[C@H:79]([NH:112][C:27](=[O:28])/[C:26](/[C:24]2[N:25]=[C:21]([NH:20][C:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=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][CH2:32][C:33]2[CH:38]=[C:37]([OH:39])[C:36]([O:40][C:41](=[O:43])[CH3:42])=[CH:35][C:34]=2[C:44]([O:46][CH:47]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)=[O:45])[C:78]3=[O:113])=[O:75])[C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13821813HCID 13821813, compoundHCID 14479181HCID 14479181, compound

Product 1

HCID 16170823HCID 16170823, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To an ice-cooled solution of the product obtained in Step 3 (0.63 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 (0.5 g) in dry dichloromethane (20 ml) was added dicyclohexylcarbodiimide (0.178 g), and the mixture was stirred overnight at room temperature. After filtering off the insoluble matters, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, giving 0.15 g of the objective compound.

Workup

  1. filtrationAfter filtering off the insoluble matters
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-68e7a7ef80fb4df7bc1efe82d5aef4b5
Source dataset
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04956474

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes