Ammonium → HCID 15024317, compound

HRID 272790

Reaction equation

HRID 272790 reaction equation
C([NH:18][C@H:19]([C:32]([OH:34])=O)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:23][CH:22]=1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[NH4+].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.[N:51]1C=CC=CC=1>O1CCOCC1.C(OCC)(=O)C.ClCCl.C(NCC)C>[C:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C@@H:19]([C:32]([NH2:51])=[O:34])[NH2:18])=[CH:22][CH:23]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

9

Reactant 4

HCID 223AmmoniumHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 10895791Fmoc-L-Tyr(tBu)-OH

Product 1

HCID 15024317HCID 15024317, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneSolventHCID 8021DiethylamineSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

N-Fmoc-O-tert-butyl-tyrosine (3.27 g, 7.12 mmol) was dissolved in dioxane (15 mL). Ammonium hydrogenocarbonate (732 mg, 9.26 mmol), di-tert-butyl-dicarbonate (2.02 g, 9.26 mmol) and pyridine (0.4 mL) were added and the mixture was stirred under nitrogen atmosphere at room temperature for 12 h. It was then diluted with ethyl acetate and the organic phase was washed with brine (2×), 5% sulfuric acid (1×) and brine again. It was dried over magnesium sulfate and concentrated. The crude thus obtained (3.17 g) was dissolved in dichloromethane (50 mL) and diethylamine (10 mL). The mixture was stirred at room temperature for 12 h, concentrated under reduced pressure and purified by flash chromatography with DCM/MeOH/NH4OH (95/5/1 then 90/10/1) to give 1.37 g of the desired compound (yield=81%).

Workup

  1. washthe organic phase was washed with brine (2×), 5% sulfuric acid (1×) and brine again
  2. dry with materialIt was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude thus obtained (3.17 g)
  5. stirringThe mixture was stirred at room temperature for 12 h
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography with DCM/MeOH/NH4OH (95/5/1

Sources & evidence

ORD record
ord-b3ee7894533f4b548def05bd37831a88
Source dataset
uspto-grants-2008_11
Patent number
US07456201B2

Linked notes

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