Toluene → O-[4-oxo-4-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]butyl]-N-[1-(phenylmethyl)-1H-tetrazol-5-yl]-L-tyrosine

HRID 1759703Notes

Reaction equation

HRID 1759703 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]([NH:42][C:43]1[NH:44][CH2:45][CH2:46][CH2:47][N:48]=1)[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:41]=[CH:40][C:17]([CH2:18][C@@H:19]([C:33]([O:35]C(C)(C)C)=[O:34])[NH:20][C:21]2[N:25]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:24]=[N:23][N:22]=2)=[CH:16][CH:15]=1.C1(C)C=CC=CC=1>ClCCl>[O:8]=[C:9]([NH:42][C:43]1[NH:44][CH2:45][CH2:46][CH2:47][N:48]=1)[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:41]=[CH:40][C:17]([CH2:18][C@@H:19]([C:33]([OH:35])=[O:34])[NH:20][C:21]2[N:25]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:24]=[N:23][N:22]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 69733081(1,1-dimethyl ethyl) O-[4-oxo-4-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]butyl]-N-[1-(phenylmethyl)-1H-tetrazol-5-yl]-L-tyrosinate

Product 1

HCID 69709932O-[4-oxo-4-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]butyl]-N-[1-(phenylmethyl)-1H-tetrazol-5-yl]-L-tyrosineYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 ml of trifluoroacetic acid is added to 135 mg of ester 5-2 in 5 ml of dichloromethane, followed by agitating for 3 hours at ambient temperature, adding 10 ml of toluene, evaporating under reduced pressure, taking up in dichloromethane and crystallizing by adding an Et2O/pentane mixture. 92 mg of 5-3 is obtained.

Workup

  1. customevaporating under reduced pressure
  2. customcrystallizing
  3. additionby adding an Et2O/pentane mixture

Sources & evidence

ORD record
ord-28322fdf5c104d5bb8e3b5414ceec5be
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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