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Methyl chloroformate → 3(R)-t-Butoxycarbonylamino-2,3,4,5-tetrahydro-1-[[2'-[[(methoxycarbonyl)amino]methyl][1,1'-biphenyl]-4-yl]-methyl]-1H-benzazepin-2-one

HRID 1740260
ノート
印刷プレビュー

反応式

HRID 1740260 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH2:33][NH2:34])=[CH:23][CH:22]=2)[C:10]1=[O:35])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:37]([O:39][CH3:40])=[O:38].C(OCC)(=O)C>C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH2:33][NH:34][C:37]([O:39][CH3:40])=[O:38])=[CH:25][CH:26]=2)[C:10]1=[O:35])=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6586Methyl chloroformateHCID 8857Ethyl AcetateHCID 228774603(R)-t-Butoxycarbonylamino-2,3,4,5-tetrahydro-1-[[2'-aminomethyl[1,1'-biphenyl]-4-yl]methyl]-1H-benzazepin-2-one

生成物 1

HCID 228774633(R)-t-Butoxycarbonylamino-2,3,4,5-tetrahydro-1-[[2'-[[(methoxycarbonyl)amino]methyl][1,1'-biphenyl]-4-yl]-methyl]-1H-benzazepin-2-one収率 95%

試薬・触媒・溶媒 2

HCID 8471
Triethylamine
触媒
HCID 6344Dichloromethane溶媒

実験手順

A solution of 31 mg (0.066 mmol) of the intermediate obtained in Step C in 1 mL of methylene chloride at room temperature was treated with 1 drop of triethylamine followed by 5 μL (6 mg, 0.067 mmol, 1 eq.) of methyl chloroformate. The mixture was stirred at room temperature for 1 hour then diluted into 10 mL of ethyl acetate and washed with 5% aqueous citric acid and saturated aqueous sodium chloride. The organic layer was removed, dried over magnesium sulfate, filtered and solvents removed under vacuum. The residue was purified by medium pressure liquid chromatography on silica, eluting with 5% methanol in ethyl acetate, to give 33 mg (0.062 mmol, 95%) of the product as a colorless glass. H NMR (400 MHz, CDCl3): δ 1.38 (s, 9H), 1.91 (m, 1H), 2.43-2.60 (m, 3H), 3.62 (s, 3H), 4.26 (m, 3H), 4.68 (br t, 1H), 4.93 (d, 15 Hz, 1H), 5.18 (d, 15 Hz, 1H), 5.45 (br d, 7 Hz, 1H), 7.13-7.35 (m, 11H), 7.41 (d, 8 Hz, 1H). FAB-MS: calculated for C31H35N3O5 529; found 530 (M+H, 25%), 430 (M-BOC, 100%).

後処理

  1. washwashed with 5% aqueous citric acid and saturated aqueous sodium chloride
  2. customThe organic layer was removed
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customsolvents removed under vacuum
  6. customThe residue was purified by medium pressure liquid chromatography on silica
  7. washeluting with 5% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-0123def310214e83a59adcde89a2b960
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05968924

反応ノート

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