Tripropylamine → 1-(4-Methoxy-benzenesulfonyl)-3-(4-methoxy-benzyloxycarbonyl-amino)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic Acid Tert-Butyl Ester

HRID 1357792노트

반응식

HRID 1357792 반응식
[C:1]([O:5][C:6]([CH:8]1[CH:14](C(O)=O)[CH2:13][CH:12]=[CH:11][CH2:10][N:9]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:32]([CH2:36]CC)CCC)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.[CH3:56][O:57][C:58]1[CH:65]=[CH:64][C:61]([CH2:62][OH:63])=[CH:60][CH:59]=1>O1CCCC1>[C:1]([O:5][C:6]([CH:8]1[CH:14]([NH:32][C:36]([O:63][CH2:62][C:61]2[CH:64]=[CH:65][C:58]([O:57][CH3:56])=[CH:59][CH:60]=2)=[O:46])[CH2:13][CH:12]=[CH:11][CH2:10][N:9]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 7616TripropylamineHCID 77384-Methoxybenzyl alcoholHCID 199401P,P-Diphenylphosphinic azideHCID 155505231-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester

생성물 1

HCID 155505251-(4-Methoxy-benzenesulfonyl)-3-(4-methoxy-benzyloxycarbonyl-amino)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic Acid Tert-Butyl Ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The reaction is performed under an Argon atmosphere and exclusion of light. 1-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester (550 mg, 1.34 mmol) is dissolved in 7 ml dry Tetrahydrofuran (THF). Tripropyl amine (TPA) (280 μl, 1.47 mmol) is added and the reaction is stirred for 30 minutes at RT. Diphenyl phosphoryl azide (318 μl, 1.47 mmol) is added and the reaction is gradually heated to 40° C. for 3 h. The reaction temperature is then increased to reflux conditions for 6 h. The reaction mixture is allowed to cool to room temperature and 4-Methoxybenzylalcohol (184 μl, 1.47 mmol) is added. The reaction is heated to reflux over night. The solvent is evaporated. Flash-chromatography Hexane/Ethylacetate (2:1) afforded the product: Cal. 383.5 found (M)+ 383.0.

후처리

  1. temperaturethe reaction is gradually heated to 40° C. for 3 h
  2. temperatureThe reaction temperature is then increased
  3. temperatureto reflux conditions for 6 h
  4. temperatureto cool to room temperature
  5. temperatureThe reaction is heated
  6. temperatureto reflux over night
  7. customThe solvent is evaporated
  8. customFlash-chromatography Hexane/Ethylacetate (2:1) afforded the product

출처 및 근거

ORD 기록
ord-a68e7fd85c4f48dca9d0dc1ab925ef94
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593351B2

반응 노트

불러오는 중…