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

HRID 742918ノート

反応式

HRID 742918 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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): δ1.60 (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.

後処理

  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

出典と根拠

ORDレコード
ord-b811d7b9372f4acb9d8bd9b6e1b993cc
出典データセット
uspto-grants-1996_09
特許番号
US05554783

反応ノート

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