Water → 3-[2(R)-Benzyloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamide

HRID 1080747ノート

反応式

HRID 1080747 の反応式
FC(F)(F)C(O)=O.[CH2:8]([O:15][C@H:16]([CH3:38])[CH2:17][NH:18][C:19]([CH3:37])([CH3:36])[CH2:20][C:21]([NH:23][C@@H:24]1[CH2:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[NH:26][C:25]1=[O:35])=[O:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:8]([O:15][C@H:16]([CH3:38])[CH2:17][NH:18][C:19]([CH3:37])([CH3:36])[CH2:20][C:21]([NH:23][C@@H:24]1[CH2:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[NH:26][C:25]1=[O:35])=[O:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 228679093-[2(R)-benzyloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamide trifluoroacetate

生成物 1

HCID 186514253-[2(R)-Benzyloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamide収率 95.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2.03 g (3.788 mmol) of 3-[2(R)-benzyloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamide trifluoroacetate (Example 10, Step B) in 40 mL of methylene chloride was added 40 mL of water. The mixture was stirred vigorously while sufficient solid potassium carbonate was added to adjust the pH of the aqueous layer to 10-11. Stirring was discontinued and the layers allowed to separate. The organic layer was removed and the aqueous layer extracted twice more with methylene chloride. The combined extracts were dried over potassium carbonate, filtered and solvents removed under vacuum to afford 1.53 g (3.62 mmol, 95%) of the product as a white solid. 1H NMR (400 MHz, DMSO-d6): 1.04 (s, 3H), 1.06 (s, 3H), 1.14 (d, 7 Hz, 3H), 1.90 (m, 1H), 2.21 (m,3H), 2.60 (m,4H), 3.59 (m,1H), 4.23 (m,1H), 4.45 (d,10 Hz,1H),4.53 (d,10 Hz,1H),6.99 (d,8 Hz,1H), 7.12 (t,8 Hz,1H), 7.20-7.35 (m,7H), 8.72 (d,8 Hz,1H), 9.79 (s,1H).

後処理

  1. additionwas added
  2. customto separate
  3. customThe organic layer was removed
  4. extractionthe aqueous layer extracted twice more with methylene chloride
  5. dry with materialThe combined extracts were dried over potassium carbonate
  6. filtrationfiltered
  7. customsolvents removed under vacuum

出典と根拠

ORDレコード
ord-02731cdb02214cdfb0d9926be7f149d8
出典データセット
uspto-grants-1996_12
特許番号
US05583130

反応ノート

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