Sodium Iodide → HCID 19389035, 화합물

HRID 1757798노트

반응식

HRID 1757798 반응식
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Br[CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].CN(C)[C:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][C:49]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:33]1([CH2:32][O:31][C:29](=[O:30])[CH2:28][N:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]=2)[CH2:28][C:29](=[O:30])[O:31][CH2:41][C:50]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 4457732HCID 4457732, 화합물

생성물 1

HCID 19389035HCID 19389035, 화합물수율 69%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 5.5 g (0.015 mol) of 3-(octadecyloxy)benzenamine, 7.3 ml (0.046 mol) of benzyl bromoacetate, 8.2 g (0.038 mol) of 1,8-bis(dimethylamino)naphthalene, 0.64 g (4.26 mmol) of sodium iodide in 100 ml of anhydrous acetonitrile and 25 ml of anhydrous DMF was stirred atreflux under an argon atmosphere for 48 hours. The solvents were removed atreduced pressure and the residue was dissolved in ethyl acetate and washed with 0.05N HCl, with saturated NaHCO3 solution dried and concentratedat reduced pressure. Purification by HPLC using 15% ethyl acetate-hexane gave, after recrystallization of the combined pure fractions from ether-hexane, 6.56 g (69% yield, mp 55°-57°) of N-[3-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

후처리

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 0.05N HCl, with saturated NaHCO3 solution
  4. customdried
  5. customPurification by HPLC
  6. customgave

출처 및 근거

ORD 기록
ord-22d5491e9f614d9ea2f866f852730dfe
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05446189

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