Dicyclohexylcarbodiimide → HCID 178460477, 화합물

HRID 555198노트

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HRID 555198 반응식
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:37][N:38]([CH3:75])[C:39]1[CH:44]=[CH:43][C:42](/[N:45]=[N:46]/[C:47]2[CH:52]=[CH:51][C:50](/[N:53]=[N:54]/[C:55]3[C:66]4[C:67]5[C:58]([NH:59][CH:60]([C:68]6[CH:73]=[CH:72][C:71](O)=[CH:70][CH:69]=6)[NH:61][C:62]=5[CH:63]=[CH:64][CH:65]=4)=[CH:57][CH:56]=3)=[CH:49][CH:48]=2)=[CH:41][CH:40]=1>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:71]2[CH:70]=[CH:69][C:68]([CH:60]3[NH:59][C:58]4[C:67]5[C:66]([C:55](/[N:54]=[N:53]/[C:50]6[CH:51]=[CH:52][C:47](/[N:46]=[N:45]/[C:42]7[CH:41]=[CH:40][C:39]([N:38]([CH3:75])[CH3:37])=[CH:44][CH:43]=7)=[CH:48][CH:49]=6)=[CH:56][CH:57]=4)=[CH:65][CH:64]=[CH:63][C:62]=5[NH:61]3)=[CH:73][CH:72]=2)=[O:18])=[CH:20][CH:21]=1)(=[O:4])[CH:2]=[CH2:3]

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 178482874HCID 178482874, 화합물

생성물 1

HCID 178460477HCID 178460477, 화합물수율 96.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To an ice cooled solution of 1.47 g of 4-{[6-(acryloyloxy)hexyl]oxy}benzoic acid (5.00 mM) and 0.24 g of DMAP (2.00 mM) in 20 ml of dichloromethane, was added a solution of 1.03 g of DCC (5.00 mM) in 10 ml of dichloromethane dropwise. After complete addition (within 15 min) stirring was continued at 0° C. for further 90 min., then 2.57 g of 4-{6-[(E)-(4-{(E)-[4-(dimethylamino)phenyl]diazenyl}phenyl)-diazenyl]-2,3-dihydro-1H-perimidin-2-yl}-phenol (5.00 mM) were added to the reaction mixture which is further stirred for 3 h at room temperature. The obtained dark-brown mixture was filtered through a pad of 20 g of celite filter aid, the cake was washed with 60 ml of dichloromethane and the filtrate was concentrated to approximately ⅓, followed by precipitation with cyclohexane/hexane 50 ml/50 ml. The obtained brown precipitate was filtered off, washed with 10 ml of hexane and dried to give 3.80 g (4.80 mM, 96%) of 4-{6-[(E)-(4-{(E)-[4-(dimethylamino)phenyl]diazenyl}phenyl)diazenyl]-2,3-dihydro-1H-perimidin-2-yl}phenyl 4-{[6-(acryloyloxy)hexyl]oxy}benzoate dark-brown powder; λmax=547 nm, ε=53000 (THF). For total purification, the dye might be flash chromatographed on silica gel.

후처리

  1. additionAfter complete addition (within 15 min)
  2. stirringis further stirred for 3 h at room temperature
  3. filtrationThe obtained dark-brown mixture was filtered through a pad of 20 g of celite
  4. filtrationfilter aid
  5. washthe cake was washed with 60 ml of dichloromethane
  6. concentrationthe filtrate was concentrated to approximately ⅓,
  7. customfollowed by precipitation with cyclohexane/hexane 50 ml/50 ml
  8. filtrationThe obtained brown precipitate was filtered off
  9. washwashed with 10 ml of hexane
  10. customdried

출처 및 근거

ORD 기록
ord-7dea942669c84afbba076b0b7efa342e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053039B2

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