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

HRID 1249712ノート

反応式

HRID 1249712 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-454c8bce0d5a4ed9ae53bd10a710313f
出典データセット
uspto-grants-2002_01
特許番号
US06335329B1

反応ノート

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