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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86687794, 화합물

HRID 926811
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HRID 926811 반응식
[C:1]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([C:19]([NH:21][C@H:22]([C:27]([NH:29][CH2:30][C:31]([OH:33])=O)=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[SH:34][C:35]1[S:36][CH2:37][CH2:38][N:39]=1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([C:19]([NH:21][C@H:22]([C:27]([NH:29][CH2:30][C:31]([N:39]1[CH2:38][CH2:37][S:36][C:35]1=[S:34])=[O:33])=[O:28])[CH2:23][CH:24]([CH3:25])[CH3:26])=[O:20])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:9])(=[O:5])[C:2]([CH3:4])=[CH2:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 54174764N-(2-Methylacryloyl)glycyl-L-phenylalanyl-L-leucylglycineHCID 178527880HCID 178527880, 화합물

생성물 1

HCID 86687794HCID 86687794, 화합물수율 51.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매
2회

반응 조건

온도
-10 °C

실험 절차

The synthesis of MA-GFLG-TT followed a published procedure [V. {hacek over (S)}ubr et al., Reactive & Functional Polymers 66 1525-1538 (2006)] with a slight modification. Under nitrogen atmosphere, N-methacryloylglycylphenylalanylleucylglycine (MA-GFLG-OH; 320 mg, 0.7 mmol), 2-mercaptothiazoline (83.5 mg, 0.7 mmol) and DMAP (85.5 mg, 0.7 mmol) were dissolved in dichloromethane (DCM) (20 mL). The solution was stirred for 5 min −10° C., EDCI (134.2 mg, 0.7 mmol) was added and the solution was stirred −10° C. for 3 h and at room temperature for another 12 h. After reaction, 50 mL DCM was added, the solution was washed with NaHCO3 aq. (0.1 M), HCl (0.1 M) and then NaCl aq. The organic layer was dried (MgSO4), solvent removed by rotary evaporation and the crude product was purified by column chromatography (silica gel 60 Å, 200-400 mesh, EtOAc: CH3OH, 15:1) and then recrystallized from DCM to give yellow powder in 51.9% yield. The structure was confirmed by 1H NMR and 13C NMR spectroscopy. 1H NMR (300 MHz, CDCl3, δ in ppm): 0.86 (m, 6 H, CH(CH3)2), 1.51 (m, 2H, CHCH2CH(CH3)2), 1.66 (m, 1H, CH(CH3)2), 1.91 (s, 3 H, CCH3), 3.03 (m, 2 H, Ph-CH2), 3.33 (t, 2 H, SCH2), 4.00 (s, 2 H, NHCH2CO), 4.54 (t, 2 H, NCH2CH2S), 4.63 (m, 1 H, NHCHCO), 4.73 (m, 1 H, NHCHCO), 4.81 (s, 2 H, NHCH2CO), 5.39 (s, 1H, C═CH2), 5.77 (s, 1H, C═CH2), 6.99 (s, 1 H, NH), 7.18 (m, 6 H, NH, Ph-H), 7.56-7.80 (m, 2 H, NH). 13C NMR (75 MHz, CDCl3, δ in ppm): 201.78, 172.6, 170.92, 170.57, 169.33, 168.99, 139.02, 136.46, 129.77, 128.80, 127.21, 121.31, 56.11, 54.89, 51.83, 46.85, 43.61, 41.81, 39.37, 29.37, 24.88, 22.86, 18.21.

후처리

  1. customThe synthesis of MA-GFLG-TT
  2. additionwas added
  3. additionwas added
  4. washthe solution was washed with NaHCO3 aq. (0.1 M), HCl (0.1 M)
  5. dry with materialNaCl aq. The organic layer was dried (MgSO4), solvent
  6. customremoved by rotary evaporation
  7. customthe crude product was purified by column chromatography (silica gel 60 Å, 200-400 mesh, EtOAc: CH3OH, 15:1)
  8. customrecrystallized from DCM
  9. customto give yellow powder in 51.9% yield

출처 및 근거

ORD 기록
ord-f17762da6f69470b888b6cbeea1ee635
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09289510B2

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