HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dicyclohexylcarbodiimide → HCID 88499001, compound

HRID 477527
Notes
Print preview

Reaction equation

HRID 477527 reaction equation
[C:1]1([C:7]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]([C:34]3[O:35][CH:36]=[CH:37][CH:38]=3)=[O:33])/[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:39]1([CH:45]([O:52][C:53]([C:55]2[N:56]3[C@H:59]([S:60][CH2:61][C:62]=2[CH2:63][S:64][C:65]2[N:70]4[N:71]=[C:72]([C:74]([O:76][CH:77]([C:84]5[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=5)[C:78]5[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=5)=[O:75])[N:73]=[C:69]4[N:68]=[C:67]([CH3:90])[CH:66]=2)[C@H:58]([NH2:91])[C:57]3=[O:92])=[O:54])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:39]1([CH:45]([O:52][C:53]([C:55]2[N:56]3[C@H:59]([S:60][CH2:61][C:62]=2[CH2:63][S:64][C:65]2[N:70]4[N:71]=[C:72]([C:74]([O:76][CH:77]([C:84]5[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=5)[C:78]5[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=5)=[O:75])[N:73]=[C:69]4[N:68]=[C:67]([CH3:90])[CH:66]=2)[C@H:58]([NH:91][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:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[S:22][CH:23]=2)=[N:30]\[O:31][C:32]([C:34]2[O:35][CH:36]=[CH:37][CH:38]=2)=[O:33])[C:57]3=[O:92])=[O:54])[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13821813HCID 13821813, compoundHCID 14850390HCID 14850390, compound

Product 1

HCID 88499001HCID 88499001, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

Conditions

Temperature
-30 °C

Procedure

The product obtained in Example 29 (3.1 g) and the product obtained in Example 15 (4.3 g) were dissolved in anhydrous dichloromethane (200 ml) with stirring, the faint yellow solution was cooled to -30° C., and a solution of dicyclohexylcarbodiimide (1.2 g) in anhydrous dichloromethane (30 ml) was dropwise added over a period of five minutes. The resulting faint yellow solution was allowed to stand at 0° C. for nine hours, the colorless crystals separated were removed by filtration, and the filtrate was washed with 50 ml of 1N aqueous citric acid, 50 ml of saturated sodium bicarbonate solution and 80 ml of saturated sodium chloride solution in that order and dried over anhydrous sodium sulfate. The dried filtrate was concentrated in vacuo, the yellow, viscous residue (6.8 g) was purified by silica gel column chromatography using ethyl acetate/n-hexane as eluent, yielding 5.3 g of the objective compound as faint yellow crystals.

Workup

  1. customthe colorless crystals separated
  2. customwere removed by filtration
  3. washthe filtrate was washed with 50 ml of 1N aqueous citric acid, 50 ml of saturated sodium bicarbonate solution and 80 ml of saturated sodium chloride solution in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried filtrate was concentrated in vacuo
  6. customthe yellow, viscous residue (6.8 g) was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-da0aa882333f40deb85f391431eb1a3b
Source dataset
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04888332

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes