Triethylamine → (R)-benzyl 4-(dimethylamino)-3-(6-phenoxypyridine-3-sulfonamido)butanoate

HRID 1958717ノート

反応式

HRID 1958717 の反応式
[NH2:1][C@@H:2]([CH2:14][N:15]([CH3:17])[CH3:16])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].C(N(CC)CC)C.[O:25]([C:32]1[N:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:17][N:15]([CH3:16])[CH2:14][C@H:2]([NH:1][S:38]([C:35]1[CH:36]=[N:37][C:32]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:33][CH:34]=1)(=[O:39])=[O:40])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 27764996-Phenoxypyridine-3-sulphonyl chlorideHCID 46223508(R)-benzyl 3-amino-4-(dimethylamino)butanoate

生成物 1

HCID 86641216(R)-benzyl 4-(dimethylamino)-3-(6-phenoxypyridine-3-sulfonamido)butanoate収率 37%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (R)-benzyl 3-amino-4-(dimethylamino)butanoate (32 mg, 0.086 mmol), triethylamine (50 μL, 0.36 mmol) and DMAP (1 mg, 0.008 mmol) in anhydrous CH2Cl2 (1 mL) was added 6-phenoxypyridine-3-sulfonyl chloride is reacted with R-aminocarnitine benzyl ester (67 mg, 0.25 mmol). The solution was stirred overnight at room temperature. The solvents were removed in vacuo and the residue was purified by preparatory HPLC. The residue was dissolved into CH2Cl2 (50 mL) and washed with 0.1 N NaOH (5 mL), dried over MgSO4 and concentrated to give the title compound as a white solid (18 mg, 37%). MS ESI 470.2 [M+H]+, calcd for [C24H27N3O5S+H]+ 470.17.

後処理

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by preparatory HPLC
  3. dissolutionThe residue was dissolved into CH2Cl2 (50 mL)
  4. washwashed with 0.1 N NaOH (5 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-27259aa0d0d2491cac48a051db30f0f0
出典データセット
uspto-grants-2013_04
特許番号
US08410150B2

反応ノート

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