Hydrochloric Acid → HCID 131714646, compound

HRID 1381165Notes

Reaction equation

HRID 1381165 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15](Cl)=[O:16])=[CH:10][C:9]=2[CH3:18])=[O:7])=[CH:4][CH:3]=1.[O-2].[Mg+2].[NH2:23][C@H:24]([C:30]([OH:32])=[O:31])[CH2:25][CH2:26][C:27](=[O:29])[NH2:28].Cl>O1CCOCC1.O>[OH2:7].[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([NH:23][C@H:24]([C:30]([OH:32])=[O:31])[CH2:25][CH2:26][C:27](=[O:29])[NH2:28])=[O:16])=[CH:10][C:9]=2[CH3:18])=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5961L-GlutamineHCID 6850729Magnesium monoxideHCID 23323832HCID 23323832, compound

Product 1

HCID 131714646HCID 131714646, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 30.5 g (0.1 mole) of [5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]-acetyl chloride in 150 ml of dioxane was added slowly at 0°-5° C. to a suspension of 5.88 g (0.15 mole) of magnesium oxide and 14.3 g (0.1 mole) of L-glutamine in 300 ml of water. The resulting yellow suspension was stirred at room temperature for 64 hours. The mixture was acidified with 1N hydrochloric acid and cooled. The precipitate was collected, washed with water and air dried. It was recrystallized three times from 2-propanol to give 10.8 g of light tan solid which was subjected to chromatography on silica gel. The column was eluted with chloroform:acetic acid:methanol (95:05:4.5). The major compound bearing fraction was concentrated to dryness and the residue recrystallized from acetone, water (2:1) to give 4.5 g (10% yield) of pale yellow crystalline N-{[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]-acetyl}-glutamine, hydrate (1:1), m.p. 186°-188° C.

Workup

  1. temperaturecooled
  2. customThe precipitate was collected
  3. washwashed with water and air
  4. customdried
  5. customIt was recrystallized three times from 2-propanol
  6. customto give 10.8 g of light tan solid which
  7. washThe column was eluted with chloroform:acetic acid:methanol (95:05:4.5)
  8. concentrationThe major compound bearing fraction was concentrated to dryness
  9. customthe residue recrystallized from acetone, water (2:1)

Sources & evidence

ORD record
ord-03c7fd00d4654a1a9d0970b4e5be3a03
Source dataset
uspto-grants-1986_04
Patent number
US04585784

Reaction notes

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