Hydrochloric Acid → 3-(L-gamma-glutamylamino)benzoic acid

HRID 705450ノート

反応式

HRID 705450 の反応式
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:8]([O:10]C(C)(C)C)=[O:9])[CH2:3][CH2:4][C:5](=O)[OH:6].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:46][C:47]1[CH:48]=[C:49]([CH:55]=[CH:56][CH:57]=1)[C:50]([O:52]CC)=[O:51].O.[OH-].[Li+].[OH-].[Li+].Cl>CN(C=O)C.O.C(O)C.C(N(CC)CC)C>[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([NH:46][C:47]1[CH:48]=[C:49]([CH:55]=[CH:56][CH:57]=1)[C:50]([OH:52])=[O:51])=[O:6]

参加物

11

反応物 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11400Ethyl 3-aminobenzoateHCID 168937Lithium hydroxide, monohydrateHCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 98382053-(L-gamma-glutamylamino)benzoic acid収率 61%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

Boc-Glu-OtBu (100 mg, 0.33 mmol) and HATU (150.4 mg, 0.40 mmol) were dissolved in 2 mL of DMF. Triethylamine (68.5 μL) was added thereto and stirred for 10 minutes. Ethyl 3-aminobenzoate (49.2 mg, 0.33 mmol) was added thereto and stirred overnight. After liquid separation was conducted with an ethyl acetate and an aqueous solution of 1M sodium hydroxide, the organic layer was washed with an aqueous solution of 1M sodium hydroxide, 1M hydrochloric acid and a saturated saline solution, successively, and dried with sodium sulfate to remove a solvent. The obtained residue was dissolved in 2 mL of THF, 1 mL of ethanol and 1 mL of water, and lithium hydroxide monohydrate (13.5 mg, 0.32 mmol) was added thereto. After stirring the mixture for 5 hours, 4.5 mg of lithium hydroxide was added thereto and stirred overnight. After confirming the completion of the reaction, pH of the reaction solution was adjusted to 2 with 1M hydrochloric acid, and a solvent was removed therefrom. 3 mL of TFA was added to the obtained residue and stirred at room temperature for 5 hours. After removing a solvent, purification was conducted in accordance with the purification process A to obtain a title compound.

後処理

  1. stirringstirred overnight
  2. customAfter liquid separation
  3. washan aqueous solution of 1M sodium hydroxide, the organic layer was washed with an aqueous solution of 1M sodium hydroxide, 1M hydrochloric acid
  4. dry with materiala saturated saline solution, successively, and dried with sodium sulfate
  5. customto remove a solvent
  6. dissolutionThe obtained residue was dissolved in 2 mL of THF
  7. stirringAfter stirring the mixture for 5 hours
  8. stirringstirred overnight
  9. customthe completion of the reaction, pH of the reaction solution
  10. customa solvent was removed
  11. addition3 mL of TFA was added to the obtained residue
  12. stirringstirred at room temperature for 5 hours
  13. customAfter removing
  14. customa solvent, purification

出典と根拠

ORDレコード
ord-30daddfd4d234cf6be87248723ce3b70
出典データセット
uspto-grants-2015_11
特許番号
US09174932B2

反応ノート

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