Hydrochloric Acid → HCID 69867781, compound

HRID 430956Notes

Reaction equation

HRID 430956 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])=O.[NH2:12][C@H:13]([C:19]([OH:21])=[O:20])[CH2:14][CH2:15][C:16](=[O:18])[NH2:17].[BH4-].[Na+].Cl>C(O)C.[OH-].[Na+]>[C:16]([CH2:15][CH2:14][C@H:13]([NH:12][CH2:1][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[C:19]([OH:21])=[O:20])(=[O:18])[NH2:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5961L-GlutamineHCID 8406Phthalaldehydic acid2×HCID 4311764Sodium borohydride2×

Product 1

HCID 69867781HCID 69867781, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
20 °C

Procedure

A suspension of 1.65 g 2-formylbenzoic acid in 5 ml ethanol and 5 ml 2 M sodium hydroxide solution was added to a solution of 1.46 g L-glutamine in 5 ml of a 2 M aqueous sodium hydroxide solution. After stirring for 1 h at 20° C., the mixture was cooled to 0° C. and 0.25 g sodium borohydride were added in portions over 15 min with vigorous stirring. After 90 min a further 0.33 g 2-formyl benzoic acid and 0.05 g sodium borohydride were added. After stirring for 16 h at 20° C., the reaction mixture was acidified with conc. hydrochloric acid to pH 2 and cooled to 0° C. The precipitate formed was separated off, washed with acetone and dried in vacuo. 0.87 g (31% of theoretical) of the title compound remained in the form of crystals, which melted at 132-133° C.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. stirringAfter stirring for 16 h at 20° C.
  3. temperaturecooled to 0° C
  4. customThe precipitate formed
  5. customwas separated off
  6. washwashed with acetone
  7. customdried in vacuo

Sources & evidence

ORD record
ord-03e8049e682b468f9bb3f9ad0f45d548
Source dataset
uspto-grants-2003_12
Patent number
US06656937B2

Reaction notes

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