Hydrochloric Acid → HCID 20622811, compound

HRID 2121220Notes

Reaction equation

HRID 2121220 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[CH:6][C:5]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Li+].Cl.Cl.[CH3:30][O:31][C:32](=[O:39])[C@H:33]([CH2:35][CH2:36][S:37][CH3:38])[NH2:34].ON1C(=O)C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CO.C(OCC)(=O)C.N1C=CC=CC=1.C1COCC1>[CH3:30][O:31][C:32](=[O:39])[C@H:33]([CH2:35][CH2:36][S:37][CH3:38])[NH:34][C:3](=[O:2])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[CH:6][C:5]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 54568565HCID 54568565, compound

Product 1

HCID 20622811HCID 20622811, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 280B (446 mg, 1.3 mmol) and aqueous saturated lithium hydroxide (3 mL) in methanol (5 mL) was heated at 60° C. for 15 hours. The reaction mixture was then neutralized with hydrogen chloride (4 N in dioxane, 5 mL). The reaction mixture was concentrated in vacuo to dryness. To the residue was added sequentially L-methionine methyl ester hydrochloride (311 mg, 1.56 mmol), 3-hydroxy 1,2,3-benzotriazin-4(3H)-one (318 mg, 1.95 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodimide (374 mg, 1.95 mmol), THF (10 mL) and pyridine (1 mL). After 15 hours, the reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was then purified by column chromatography (ethyl acetate) to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-d30f093b1e4c4bffbabaa70415dca66f
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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