Hydrochloric Acid → HCID 15928542, compound

HRID 339227Notes

Reaction equation

HRID 339227 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[C:11]([I:13])[C:10]([OH:14])=[C:9]([I:15])[CH:8]=1)[C:3]([OH:5])=[O:4].[CH2:16]=O.Cl>COCCOC>[OH:14][C:10]1[C:9]([I:15])=[C:8]2[C:7]([CH2:6][C@@H:2]([C:3]([OH:5])=[O:4])[NH:1][CH2:16]2)=[CH:12][C:11]=1[I:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 93053',5'-Diiodo-L-tyrosine

Product 1

HCID 15928542HCID 15928542, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
72 °C

Procedure

A thick-walled reaction flask with a screw top was charged sequentially with (S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid (Chem-Impex Int'l Inc., 5.0 g, 12 mmol), 1,2-dimethoxyethane (5.0 mL), formaldehyde (37% wt. in H2O, 4.5 mL, 60 mmol), and conc. HCl (60.2 mL, 1981 mmol). The resulting tan slurry was sealed with a screw top and heated to 72° C. slowly over 30 min and then maintained at 72° C. for 12 h. The resulting brown reaction slurry was then cooled to 0° C., filtered while cold, and washed with small amounts of 1,2-dimethoxyethane to give the title compound (2.42 g, 5.45 mmol, 47%) as a white solid. 1H NMR (DMSO-d6) δ 9.93 (br s, 1H), 9.69 (br s, 1H), 7.75 (s, 1H), 4.34 (d, J=7.7 Hz, 1H), 4.21-3.94 (m, 2H), 3.93-3.47 (m, 1H), 3.33-3.16 (m, 1H), 3.15-2.97 (m, 1H); MS (ESI+) m/z 445.9 (M+H)+.

Workup

  1. customThe resulting tan slurry was sealed with a screw top
  2. temperaturemaintained at 72° C. for 12 h
  3. temperatureThe resulting brown reaction slurry was then cooled to 0° C.
  4. filtrationfiltered while cold, and
  5. washwashed with small amounts of 1,2-dimethoxyethane

Sources & evidence

ORD record
ord-9c8592d8e8a9413388382d24454b37d7
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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