Triethylamine → HCID 54546551, compound

HRID 1729100Notes

Reaction equation

HRID 1729100 reaction equation
[C:1](Cl)(=[O:13])[O:2][CH:3]1[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.[CH3:15][C:16]([NH2:29])([C:25]([O:27][CH3:28])=[O:26])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.Cl.CCOC(C)=O.C(N(CC)CC)C>C1COCC1>[CH3:15][C:16]([C:25]([O:27][CH3:28])=[O:26])([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[NH:29][C:1]([O:2][CH:3]1[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2)=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 108785372-adamantyl ChloroformateHCID 11957616DL-alpha-Methyltyrosine methyl ester hydrochloride

Product 1

HCID 54546551HCID 54546551, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of tricyclo[3.3.1.13,7 ]dec-2-yl carbonchloridate [5.77 g, 0.026 mmol, prepared from 2-adamantanol and his (trichloromethyl)carbonate (Horwell, D. C., et al, J. Med. Chem. 1991, 34,404-414)] in 60 mL THF, a solution of DL-α-methyltyrosine methyl ester (5.0 g, 0.0238 mol, prepared from the DL-α-methyltyrosine methyl ester hydrochloride using 1M K2CO3 and EtOAc) in 320 mL THF was added dropwise via an addition funnel, keeping the temperature below 25° C. A solution of triethylamine (4.81 g, 0.047 mol) in 120mL THF was then added dropwise and the heterogeneous reaction mixture was stirred for 16 hours at room temperature under a nitrogen atmosphere. The amine salt was filtered and the filtrate was concentrated in vacuo to givea tan, fluffy solid. Purification by flash chromatography (silica gel, 10% EtOAc/hexane) yielded the title compound. MS: 388 (MH+); 387 (M+).

Workup

  1. additionwas added dropwise via an addition funnel
  2. customthe temperature below 25° C
  3. filtrationThe amine salt was filtered
  4. concentrationthe filtrate was concentrated in vacuo to givea tan, fluffy solid
  5. customPurification by flash chromatography (silica gel, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-043195ff97404792bc01d576bf4508d5
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

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