Hydrochloric Acid → Boc-Asp(OcHex) 2-aminomethylphenylacetic Acid

HRID 1417890Notes

Reaction equation

HRID 1417890 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11].Cl.C([O-])(O)=O.[Na+].[NH:19]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:20]([C:31]([O:33]N1C(=O)CCC1=O)=[O:32])[CH2:21][C:22](=[O:30])[O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>O.C1COCC1>[NH:19]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:20]([C:31]([OH:33])=[O:32])[CH2:21][C:22](=[O:30])[O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 1514158(2-(Aminomethyl)phenyl)acetic acidHCID 14162316Boc-Asp(OcHex)-OSu

Product 1

HCID 131721147Boc-Asp(OcHex) 2-aminomethylphenylacetic AcidYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-aminomethylphenylacetic acid.HCl (4.0 g, 20 mmol) in H2O (20 ml) was added NaHCO3 (5.0 g, 60 mmol), followed by a solution of Boc-Asp(OcHex)-OSu (7.5 g, 18 mmol) in THF (20 ml). The reaction mixture was stirred at room temperature for 3 hours, filtered, diluted with H2O, acidified with 1N HCl, and extracted with ethyl acetate. The extracts were washed with H2O, brine, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. This material was triturated with ether to provide the title compound (7.0 g, 83%) as a white powder. 1H NMR (D6 -DMSO) 12.40 (br s, 1H), 8.30 (br t, 1H), 7.20 (m, 5H), 4.65 (m, 1H), 4.35 (q, 1H), 4.25 (m, 2H), 3.65 (s, 2H), 2.70 (dd, 1H), 2.55 (dd, 1H), 1.70 (m, 4H), 1.40 (s, 9H), 1.35 (m, 6H).

Workup

  1. filtrationfiltered
  2. additiondiluted with H2O
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with H2O, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThis material was triturated with ether

Sources & evidence

ORD record
ord-70162722d2864afb8088acaff6d772be
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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