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

HRID 1958717노트

반응식

HRID 1958717 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-27259aa0d0d2491cac48a051db30f0f0
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410150B2

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