Water → HCID 53668792, compound

HRID 1418797Notes

Reaction equation

HRID 1418797 reaction equation
[C:1]([O:5][C:6](=[O:24])[C@H:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].O.C(=O)([O-])[O-].[K+].[K+].[C:32]([O:36][C:37](=[O:40])[CH2:38]Br)([CH3:35])([CH3:34])[CH3:33]>O1CCCC1>[C:1]([O:5][C:6](=[O:24])[CH:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:38][C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:40])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 22885226HCID 22885226, compound

Product 1

HCID 53668792HCID 53668792, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.1 g (46.1 mmol) of N-benzyl-tyrosine-tert-butyl ester (Example i) is dissolved in 50 ml of tetrahydrofuran and mixed with 5 ml of water and 9.54 g (69 mmol) of potassium carbonate. After instillation of 9.89 g (51 mmol) of bromoacetic acid-tert-butyl ester, it is stirred for two days at 65° C. After cooling, it is filtered, concentrated by evaporation in a vacuum and the residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine. The product fractions are concentrated by evaporation in a vacuum and dried.

Workup

  1. temperatureAfter cooling
  2. filtrationit is filtered
  3. concentrationconcentrated by evaporation in a vacuum
  4. customthe residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine
  5. concentrationThe product fractions are concentrated by evaporation in a vacuum
  6. customdried

Sources & evidence

ORD record
ord-3f2b307d1e494b5caf7fc0aa0e297420
Source dataset
uspto-grants-1999_03
Patent number
US05885548

Reaction notes

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