3-Pyridinemethanamine → 2(S),5(S)-Bis-(N-(3-pyridylmethylamino-carbonyl)-amino)-1,6-diphenyl-3(S)-hydroxyhexane

HRID 52832노트

반응식

HRID 52832 반응식
[N+](C1C=CC(O[C:9]([NH:11][C@H:12]([C@@H:20]([O:43][Si](C)(C)C)[CH2:21][C@@H:22]([NH:30][C:31]([O:33]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])=CC=1)([O-])=O.[NH2:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1>CN(C=O)C>[N:54]1[CH:55]=[CH:56][CH:57]=[C:52]([CH2:51][NH:50][C:9]([NH:11][C@H:12]([C@@H:20]([OH:43])[CH2:21][C@@H:22]([NH:30][C:31]([NH:50][CH2:51][C:52]2[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=2)=[O:33])[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:10])[CH:53]=1

참가 물질

4

반응물 2

HCID 310183-PyridinemethanamineHCID 186556462(S),5(S)-Bis-(N-(p-nitrophenoxycarbonyl)-amino)-1,6-diphenyl-3(S)-trimethylsiloxy-hexane

생성물 1

HCID 542471732(S),5(S)-Bis-(N-(3-pyridylmethylamino-carbonyl)-amino)-1,6-diphenyl-3(S)-hydroxyhexane

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 87 mg of the resultant compound from Example 218 in 1 ml of DMF was added 0.028 ml of 3-aminomethylpyridine. After 18 hours, the solvent was removed in vacuo and the residue was dissolved in 1 ml of methanol and 0.05 ml of chlorotrimethylsilane was added. After 0.5 hour, the solvent was removed in vacuo, neutralized with sodium bicarbonate solution and extraction with ethyl acetate (2×25 ml). The organic solution was dried and concentrated. Purification by silica gel column chromotography provided 35 mg of desired product. 1H NMR (CD3OD): δ 1.60 (t, 2H), 2.60-2.80 (m, 4H), 3.70 (m, 1H), 4.00 (m, 1H), 4.10 (m, 1H), 4.25-4.35 (m, 4H), 7.10-7.25 (m, 10H), 7.35 (m, 2H), 7.60 (m, 2H), 8.40 (m, 4H). Mass spectrum: (M+H)+ =553.

후처리

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 1 ml of methanol
  3. addition0.05 ml of chlorotrimethylsilane was added
  4. waitAfter 0.5 hour
  5. customthe solvent was removed in vacuo
  6. extractionneutralized with sodium bicarbonate solution and extraction with ethyl acetate (2×25 ml)
  7. customThe organic solution was dried
  8. concentrationconcentrated
  9. customPurification by silica gel column chromotography

출처 및 근거

ORD 기록
ord-711a4c518709454b851dcd292630dcd5
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616714

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