Benzyl bromoacetate → N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester

HRID 1757819노트

반응식

HRID 1757819 반응식
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[C:6]([NH2:29])[CH:5]=1.Br[CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].CN(C)[C:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][C:53]=2N(C)C)C=CC=1.[Na]>CN(C=O)C.C(#N)C>[C:37]1([CH2:36][O:35][C:33](=[O:34])[CH2:32][N:29]([C:6]2[CH:7]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:30])[CH:5]=2)[CH2:4][C:3](=[O:2])[O:30][CH2:45][C:54]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

참가 물질

7

반응물 4

HCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 5360545SodiumHCID 193890883-Amino-5-(octadecyloxy)benzoic acid methyl ester

생성물 1

HCID 19388997N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester수율 93.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 3.25 g (7.74 mmol) of 3-amino-5-(octadecyloxy)benzoic acid methyl ester, 3.7 ml (23 mmol) of benzyl bromoacetate, 4.2 g (19.4 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.3 g (2.2 mmol) of sodium iodidein 65 ml of acetonitrile and 20 ml of DMF was stirred and heated at reflux under argon for 48 hours. The reaction mixture was concentrated at reducedpressure and ethyl acetate was added to the residue. The extract was washedwith 0.05N HCl, with saturated NaHCO3 solution, dried and concentratedat reduced pressure to a solid which was purified by HPLC using 15% ethyl acetate-hexane to give 2.6 g (48% yield, mp 62°-63°) of N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy) ethyl]glycine phenylmethyl ester.

후처리

  1. temperatureheated
  2. temperatureat reflux under argon for 48 hours
  3. concentrationThe reaction mixture was concentrated at reducedpressure and ethyl acetate
  4. additionwas added to the residue
  5. customdried
  6. customconcentratedat reduced pressure to a solid which was purified by HPLC

출처 및 근거

ORD 기록
ord-1801597085ba4c198290f1eed2b67f05
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05446189

반응 노트

불러오는 중…