Hydrochloric Acid → Phenylacetylglutamine

HRID 2372703Notes

Reaction equation

HRID 2372703 reaction equation
C([O:5][C:6](=[O:23])[C@H:7]([CH2:18][CH2:19][C:20](=[O:22])[NH2:21])[NH:8][C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C)(C)C.C(N(CC)CC)C.Cl>CN(C)C=O>[C:11]1([CH2:10][C:9]([NH:8][C@H:7]([C:6]([OH:23])=[O:5])[CH2:18][CH2:19][C:20](=[O:22])[NH2:21])=[O:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 53814505Phenylacetylglutamine t-butyl ester

Product 1

HCID 92258Phenylacetylglutamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As shown in Scheme III (FIG. 3), phenylacetylglutamine 5 (25 mg) from Example 1 was dissolved in dimethylformamide (500 μl), and 2-ethyl 5-phenylisoxazolium-3'-sulfonate 8 (26 mg) was added. The pH of the reaction mixture was adjusted to 9 with triethylamine. After 45 minutes, aminomethylfluorescein hydrochloride 7 (38 mg) was added, and reaction mixture was stirred for an additional 12 hours. After evaporation to dryness, the residue was dissolved in methanol and purified by preparative thin layer chromatography using reversed silica gel and water-methanol-acetic acid (40:60:0.4) as an eluent. The result was 40 mg of the desired PAG/AMF conjugate 9. Mass spectrum (FAB): 608 M+.

Workup

  1. customreaction mixture
  2. customAfter evaporation to dryness
  3. dissolutionthe residue was dissolved in methanol
  4. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-d4b5a8544c2b4d76ae6c231031bff6ad
Source dataset
uspto-grants-1992_03
Patent number
US05100807

Reaction notes

Loading…