Hydrochloric Acid → HCID 12040690, compound

HRID 1369169Notes

Reaction equation

HRID 1369169 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(N1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])(OCC)=O.C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[CH2:1]([O:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@H:9]([N:10]2[C:25](=[O:26])[C:24]3[C:23](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22]2=[O:31])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 11275812O-Ethyl-L-tyrosine

Product 1

HCID 12040690HCID 12040690, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

O-Ethyl-L-tyrosine (IV, EXAMPLE 3, 20.9 g, 100 mmol) and N-carbethoxyphthalimide (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-a91405e6b09d4ffabe9881eeee8f9c81
Source dataset
uspto-grants-2003_06
Patent number
US06576769B2

Reaction notes

Loading…