4-Methoxy-2-nitrophenyl isothiocyanate → (1,1-dimethyl ethyl) N-[[(2-amino-4-methoxyphenyl)amino]thioxomethyl]-O-(4-ethoxy-4-oxobutyl)-L-tyrosinate

HRID 1759696ノート

反応式

HRID 1759696 の反応式
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][C@@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH2:15])=[CH:11][CH:10]=1)[CH3:2].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[S:36])=[C:30]([N+:37]([O-])=O)[CH:29]=1>C1COCC1>[NH2:37][C:30]1[CH:29]=[C:28]([O:27][CH3:26])[CH:33]=[CH:32][C:31]=1[NH:34][C:35](=[S:36])[NH:15][C@H:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:25])=[CH:24][CH:23]=1

参加物

4

反応物 2

HCID 1410064-Methoxy-2-nitrophenyl isothiocyanateHCID 15512208tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate

生成物 1

HCID 86594971(1,1-dimethyl ethyl) N-[[(2-amino-4-methoxyphenyl)amino]thioxomethyl]-O-(4-ethoxy-4-oxobutyl)-L-tyrosinate収率 99.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The aminoester 4-2 (350 mg, 1 mmole) in 20 ml of THF is mixed with 4-methoxy-2-nitrophenyl isothiocyanate (210 mg, 1 mmole), followed by agitating for 1 hour at ambient temperature, evaporating under reduced pressure, then adding SnCl2 (380 mg then 190 mg, 3 mmoles) in 10 ml of DMF and agitating for 4 hours at ambient temperature. After evaporating under reduced pressure and taking up in a water/NaHCO3/AcOEt mixture, decanting, drying the organic phase and evaporating under reduced pressure, 530 mg of crude product is obtained.

後処理

  1. customevaporating under reduced pressure
  2. stirringadding SnCl2 (380 mg then 190 mg, 3 mmoles) in 10 ml of DMF and agitating for 4 hours at ambient temperature
  3. customAfter evaporating under reduced pressure
  4. customdecanting
  5. customdrying the organic phase
  6. customevaporating under reduced pressure

出典と根拠

ORDレコード
ord-0d91d8e15271485787418d66c687e1f3
出典データセット
uspto-grants-2005_01
特許番号
US06838453B2

反応ノート

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