Ammonia → HCID 59909900, compound

HRID 1280085Notes

Reaction equation

HRID 1280085 reaction equation
[C:1]([NH:8][C@H:9]([C:25]([OH:27])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC[N:30](C(C)C)C(C)C.C(OC(Cl)=O)C(C)C.N.C(O)(C)C>C1COCC1>[C:21]([O:20][C:18](=[O:19])[O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C@H:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:25](=[O:27])[NH2:30])=[CH:12][CH:13]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 3776IsopropanolHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 7010630BOC-TYR(BOC)-OH

Product 1

HCID 59909900HCID 59909900, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,O-Bis-Boc-(S)-tyrosine from example 64 (5.00 g, 13.11 mmol) was dissolved in THF (20 mL), the solution stirred under an argon atmosphere and cooled in an ice bath. DIEA (5.70 mL, 32.7 mmol) was added followed by isobutylchloroformate (2.55 mL, 19.6 mmol). After 45 min a solution of 2M ammonia in isopropanol (39.3 mL, 78.6 mmol) was added and the mixture stirred at room temperature for 18 h. The solvent was evaporated, the residue taken in EtOAC (100 mL), washed with 5% aqueous citric acid (2×50 mL), 5% aqueous sodium bicarbonate (2×50 mL) and brine. After drying (MgSO4) and evaporation of the solvent, the residue was dissolved in chloroform (15 mL), stirred vigorously and Et2O (150 mL) was added. The suspension was stirred for 20 min. then the solid filtered and air dried to yield 3.10 g (62%) of the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe mixture stirred at room temperature for 18 h
  3. customThe solvent was evaporated
  4. washwashed with 5% aqueous citric acid (2×50 mL), 5% aqueous sodium bicarbonate (2×50 mL) and brine
  5. customAfter drying
  6. custom(MgSO4) and evaporation of the solvent
  7. dissolutionthe residue was dissolved in chloroform (15 mL)
  8. stirringstirred vigorously
  9. additionEt2O (150 mL) was added
  10. stirringThe suspension was stirred for 20 min.
  11. filtrationthe solid filtered
  12. customair dried

Sources & evidence

ORD record
ord-318adc12e3fb4f8696014cfb785eaed7
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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