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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178501478, 화합물

HRID 363204
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HRID 363204 반응식
Cl.[CH3:2][O:3][C:4](=[O:32])[C@H:5]([CH2:28][CH2:29][S:30][CH3:31])[NH:6][C:7](=[O:27])[CH2:8][N:9]([CH2:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1)[CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.Cl.[NH:34]1[CH:38]=[CH:37][N:36]=[C:35]1CC(O)=O.O.[OH:44][C:45]1C2N=NNC=2C=C[CH:46]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[CH3:2][O:3][C:4](=[O:32])[C@H:5]([CH2:28][CH2:29][S:30][CH3:31])[NH:6][C:7](=[O:27])[CH2:8][N:9]([CH2:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:45](=[O:44])[CH2:46][C:37]1[N:36]=[CH:35][NH:34][CH:38]=1)[CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 532309242-(1H-imidazol-2-yl)acetic acid hydrochlorideHCID 67585810N-(pyrrolidin-2(S)-ylmethyl)-N-(1-naphthylmethyl)-glycyl-methionine methyl ester hydrochlorideHCID 178526939HCID 178526939, 화합물

생성물 1

HCID 178501478HCID 178501478, 화합물

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

N-(pyrrolidin-2(S)-ylmethyl)-N-(1-naphthylmethyl)-glycyl-methionine methyl ester hydrochloride (0.200 g, 0.387 mmol), imidazoleacetic acid hydrochloride (0.094 g, 0.581 mmol), hydroxybenzotriazole hydrate (0.086 g, 0.639 mmol), EDC hydrochloride (0.134 g, 0.697 mmol) and TEA (0.340 mL, 2.44 mmol) were dissolved in dry DMF (4 mL) and stirred under Ar for 3 h. The mixture was concentrated in vacuo and the residue taken up in aq satd NaHCO3 soln and extracted with EtOAc (2×40 mL). The organics were washed with H2O and brine, dried over MgSO4, filtered and the solvent removed in vacuo to give an oil which was chromatographed on silica gel (5:95 MeOH:CH2Cl2) to give the title compound. 1H NMR (CD3OD) δ8.32 (d, 1H, J=8 Hz), 7.90 (d, 1H, J=8 Hz), 7.83 (d, 1H, J=8 Hz), 7.39 -7.62 (m, 5H), 6.92 (br s, 1H), 4.34-4.52 (m, 3H), 3.94 (d, 1H, J=13 Hz), 3.59-3.78 (m, 2H), 3.67 (s, 3H), 3.21-3.56 (m, 6H), 2.93 (dd, 1H, J=4, 13 Hz), 2.51 (dd, 1H, J=9, 13 Hz), 2.02-2.14 (m, 1H), 1.68-2.02 (m, 6H), 1.92 (s, 3H), 1.39-1.52 (m, 1H).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe organics were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customto give an oil which
  8. customwas chromatographed on silica gel (5:95 MeOH:CH2Cl2)

출처 및 근거

ORD 기록
ord-7d811e3cfddc47d2b8ad42a6f6aebfa4
출처 데이터셋
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05872135

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