Hydrochloric Acid → HCID 12040690, compound

HRID 991278Notes

Reaction equation

HRID 991278 reaction equation
[CH2:1]([O:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)[CH3:2].[C:16](=[O:19])([O-])[O-].[Na+].[Na+].Cl.[OH2:23]>>[CH2:1]([O:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@H:9]([N:10]2[C:8](=[O:23])[C:7]3[C:6](=[CH:5][CH:4]=[CH:15][CH:14]=3)[C:16]2=[O:19])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 11275812O-Ethyl-L-tyrosine

Product 1

HCID 12040690HCID 12040690, compound

Procedure

O-Ethyl-L-tyrosine (IV. EXAMPLE 3, 20.9 g, 100 mmol) and N-carhethoxyphthalimide (23.0 g, 105 mmol) are suspended in water (210 mL). Sodium carbonate (11.1 g, 105 mmol) is added and the mixture is stirred at 20-25° for 24 hr. Hydrochloric acid (1N, 200 mL) is added to the resulting mixture and stirred for 2 hr. The mixture is filtered, washed with water (100 mL) and dried to give the title compound, NMR (MeOH-d4) δ7.78-7.72, 7.14, 6.68, 5.11, 3.90, 3.47 and 1.28; CMR (MeOH-d4) δ172.2, 169.0, 159.2, 135.6, 132.8, 130.9, 130.3, 124.2, 115.5, 64.3, 54.8, 34.7 and 15.0.

Workup

  1. stirringstirred for 2 hr
  2. filtrationThe mixture is filtered
  3. washwashed with water (100 mL)
  4. customdried

Sources & evidence

ORD record
ord-f5cd9f43986d4d469923ece178afd3f8
Source dataset
uspto-grants-2002_10
Patent number
US06462234B2

Reaction notes

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