Triethylamine → HCID 117995906, 화합물

HRID 1488269노트

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HRID 1488269 반응식
[CH2:1]([O:8][C:9](=[O:28])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:27])[CH2:17][N:18]([CH2:23][C:24]([OH:26])=O)[CH2:19][C:20]([OH:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CCN(CC)CC.[NH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:55]([NH:57][CH2:58][CH2:59][O:60][C@@H:61]1[O:69][C@@H:68]([CH3:70])[C@@H:66]([OH:67])[C@@H:64]([OH:65])[C@@H:62]1[OH:63])=[O:56]>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][C:9](=[O:28])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:27])[CH2:17][N:18]([CH2:19][C:20]([OH:22])=[O:21])[CH2:23][C:24]([NH:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:55]([NH:57][CH2:58][CH2:59][O:60][C@@H:61]1[O:69][C@@H:68]([CH3:70])[C@@H:66]([OH:67])[C@@H:64]([OH:65])[C@@H:62]1[OH:63])=[O:56])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 68077581HCID 68077581, 화합물HCID 117995908HCID 117995908, 화합물

생성물 1

HCID 117995906HCID 117995906, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a suspension of 2,2′-[(2-{[6-(benzyloxy)-6-oxohexyl]amino}-2-oxoethyl)azanediyl]diacetic acid (1.0 g, 2.54 mmol) in CH2Cl2 (30 mL) at 0° C. was added trifluoroacetic anhydride (448 μL, 3.17 mmol). After stirring at 0° C. for 3 hr, the mixture was cooled to −30° C., to which a solution of Et3N (848 μL, 6.08 mmol) in DMF (20 mL) was added dropwise over 30 mins After stirring at −30° C. for 30 min, a mixture of 6-amino-N-{2-[(α-L-fucopyranosyl)oxy]ethyl}hexanamide (812 mg, 2.54 mmol) in DMF (30 mL) was added and the resulting mixture was allowed to stir at rt. After stirring for 16 hr, the mixture was concentrated and the residue was purified by flash chromatography on C18 reverse phase silica gel (42 g), eluting with 0-40% AcCN in water to produce the title compound. UPLC Method B: m/e=697.3876 [M+1]; Rt=3.398 min. 1H NMR (CD3OD) δ 1.23 (3 H, d, J=6.59), 1.39-1.36 (4 H, m), 1.56 (6 H, s), 1.67 (6 H, d, J=10.32), 2.23 (2 H, t, J=7.50), 2.41 (2 H, t, J=7.37), 3.24 (6 H, m), 3.42 (4 H, s), 3.49 (2 H, s), 3.57-3.52 (3 H, m), 3.68 (1 H, s), 3.77 (3 H, t, J=1.65), 3.98-3.94 (1 H, m), 4.77 (1 H, s), 5.14 (2 H, s), 7.38 (5 H, d, J=4.43).

후처리

  1. additionwas added dropwise over 30 mins
  2. stirringAfter stirring at −30° C. for 30 min
  3. additionwas added
  4. stirringto stir at rt
  5. stirringAfter stirring for 16 hr
  6. concentrationthe mixture was concentrated
  7. customthe residue was purified by flash chromatography on C18 reverse phase silica gel (42 g)
  8. washeluting with 0-40% AcCN in water

출처 및 근거

ORD 기록
ord-70959328fe2b4a3c8713620445638f9b
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09427475B2

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