Hydrochloric Acid → HCID 58422556, compound

HRID 2093300Notes

Reaction equation

HRID 2093300 reaction equation
Cl.O.N[CH:4]([CH2:8]C1C=CC=CC=1)[C:5](O)=O.[CH2:15]([O:18][C:19]1[CH:30]=[CH:29][C:22]([CH2:23][C@@H:24]([C:26]([OH:28])=[O:27])[NH2:25])=[CH:21][CH:20]=1)[C:16]#[CH:17]>[OH-].[Na+].CO>[CH2:8]([O:27][C:26](=[O:28])[CH:24]([NH2:25])[CH2:23][C:22]1[CH:29]=[CH:30][C:19]([O:18][CH2:15][C:16]#[CH:17])=[CH:20][CH:21]=1)[C:4]#[CH:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 994Dl-Phenylalanine2×HCID 11252961H-L-Tyr(Propargyl)-OH

Product 1

HCID 58422556HCID 58422556, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The propargyl ester (1.6 g, 5.5 mmol) from the previous step was dissolved in a mixture of aqueous 2 N NaOH (14 mL) and MeOH (10 mL). After stirring for 1.5 h at room temperature, the pH was adjusted to 7 by adding conc. HCl. Water (20 mL) was added and the mixture was kept at 4° C. overnight. The precipitate was filtered, washed with ice-cold H2O, and dried under vacuum yielding, 1.23 g (90%) of 1 in FIG. 11 (2-Amino-3-phenylpropionic acid (1) (also known as p-propargyloxyphenylalanine) as a white solid. 1H NMR (400 MHz, D2O) (as the potassium salt in D2O) δ 7.20 (d, J=8.8 Hz, 2H), 6.99 (d, J=8.8 Hz, 2H), 4.75 (s, 2H), 3.50 (dd, J=5.6, 7.2 Hz, 1H), 2.95 (dd, J=5.6, 13.6 Hz, 1H), 2.82 (dd, J=7.2, 13.6 Hz, 1H); 13C NMR (100 MHz, D2O) δ 181.3, 164.9, 155.6, 131.4, 130.7, 115.3, 57.3, 56.1, 39.3; HRMS (CI) m/z 220.0969 [C12H13NO3 (M+1) requires 220.0968].

Workup

  1. waitthe mixture was kept at 4° C. overnight
  2. filtrationThe precipitate was filtered
  3. washwashed with ice-cold H2O
  4. customdried under vacuum
  5. customyielding

Sources & evidence

ORD record
ord-c1037a2d826c400e9e63561b4de0b6cc
Source dataset
uspto-grants-2013_05
Patent number
US08445446B2

Reaction notes

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