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Sodium Iodide → N-[3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester

HRID 1110254
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HRID 1110254 반응식
[CH3:1][O:2][C:3](=[O:35])[CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:12]=[C:11]([NH2:34])[CH:10]=1.Br[CH2:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39].CN(C)[C:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][C:58]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:42]1([CH2:41][O:40][C:38](=[O:39])[CH2:37][N:34]([C:11]2[CH:10]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:35])[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:12]=2)[CH2:4][C:3](=[O:2])[O:35][CH2:50][C:59]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 543104535-[3-Amino-5-(octadecyloxy)phenoxy]pentanoic acid methyl ester

생성물 1

HCID 19388929N-[3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester수율 120.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 6.77 g (13.8 mmol) of 5-[3-amino-5-(octadecyloxy)phenoxy]pentanoic acid methyl ester, 6.6 ml (41.3 mmol) of benzyl bromoacetate, 7.4 g (34.4 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.6 g (3.9 mmol) of sodium iodide in 150 ml of acetonitrile and 50 ml of DMF was stirred at reflux under an argon atmosphere for 48 hours. The reaction mixture was concentrated at reduced pressure to remove the solvents and ethyl acetate was added to the residue. The extract was washed with 0.5N HCl, with NaHCO3 solution, dried and concentrated at reduced pressure to an oil. Purification by HPLC using 20% ethyl acetate-hexane gave 6.55 g (60% yield, mp 48°-50°) of N-[3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

후처리

  1. temperatureat reflux under an argon atmosphere for 48 hours
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. customto remove the solvents and ethyl acetate
  4. additionwas added to the residue
  5. washThe extract was washed with 0.5N HCl, with NaHCO3 solution
  6. customdried
  7. concentrationconcentrated at reduced pressure to an oil
  8. customPurification by HPLC

출처 및 근거

ORD 기록
ord-743ab6af07614aad86a6797976b4985b
출처 데이터셋
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05324747

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