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

HRID 1759696Notes

Reaction equation

HRID 1759696 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0d91d8e15271485787418d66c687e1f3
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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