5-Aminosalicylic Acid → Boc-Lys(Z)-OH

HRID 1262487Notes

Reaction equation

HRID 1262487 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].N[C:29]1C=[C:33](C(O)=O)[C:32]([OH:38])=[CH:31]C=1.CN(C=O)C>C1COCC1>[CH3:29][CH2:21][O:23][CH2:24][CH3:27].[CH:2]([O:38][CH:32]([CH3:31])[CH3:33])([CH3:18])[CH3:3].[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

6

Reactant 3

HCID 40755-Aminosalicylic AcidHCID 6228DimethylformamideHCID 2724765Boc-Lys(Z)-OH

Product 2

HCID 2724765Boc-Lys(Z)-OHYield 55%HCID 21919906Ether isopropyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

70.4 g (0.14 mole) of BOC-L-Lys(Z)-SDP (m.w. 502.6) was dissolved in 200 ml of THF, which was then added dropwise to a solution of 21.4 g (0.14 mole) of 5-aminosalicyclic acid (m.w. 153.14) in 187 ml of 1.5 N NEM/DMF solution at 0°-5° C., and the reaction was effected at normal temperature for 18 hours, after which the reaction mixture was concentrated to 100-200 ml, 1600 ml of ether/ethyl acetate (50 v/50 v) was added, the mixture was washed with 1000 ml of cold 5% HCl three times and then with 1000 ml of saturated aqueous NaCl twice, active carbon was added, dried on magnesium sulfate, and the solvent was distilled off, to obtain, by recystallization from ether/isopropyl ether, 8.9 g (yield 55%) of crystalline BOC-L-Lys(Z)-CHA (m.w. 515.6) of m.p. 102°-105° C.

Workup

  1. concentrationafter which the reaction mixture was concentrated to 100-200 ml, 1600 ml of ether/ethyl acetate (50 v/50 v)
  2. additionwas added
  3. washthe mixture was washed with 1000 ml of cold 5% HCl three times
  4. additionwith 1000 ml of saturated aqueous NaCl twice, active carbon was added
  5. customdried on magnesium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6051c30d8fb24dafba96b2c49fca2c37
Source dataset
uspto-grants-1984_06
Patent number
US04452736

Reaction notes

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