1-Hydroxybenzotriazole → HCID 9798247, compound

HRID 990104Notes

Reaction equation

HRID 990104 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:22]=[CH:21][C:10]([CH2:11][N:12]3[CH2:16][C@H:15]([C:17](O)=[O:18])[NH:14][C:13]3=[O:20])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH:25][N:26]1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.C[Si](C)(C)CCON.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.O>[OH:25][NH:26][C:17]([C@H:15]1[CH2:16][N:12]([CH2:11][C:10]2[CH:21]=[CH:22][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:24][CH:23]=3)=[CH:8][CH:9]=2)[C:13](=[O:20])[NH:14]1)=[O:18]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12971981HCID 12971981, compoundHCID 18419632O-[2-(Trimethylsilyl)ethyl]hydroxylamine--hydrogen chloride (1/1)

Product 1

HCID 9798247HCID 9798247, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4R)-l -[4-(4-fluorophenoxy)benzyl]-2-oxo-imidazolidine-4-carboxylic acid (120 mg, 0.36 mmol) in methylene chloride (5 mL) were added sequentially 1-hydroxybenztria zole (73 mg, 0.54 mmol), diisopropylethylamine (0.13 mL, 0.75 mmol), O-(2-trimethylsilylethyl)hydroxylamine hydrochloride (92 mg, 0.54 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (104 mg, 0.54 mmol). The reaction mixture was stirred at room temperature for 16 hours and was then diluted with methylene chloride and water. The organic phase was washed successively with aqueous 1M HCI solution, water, aqueous saturated NaHCO3 solution and brine. After drying over MgSO4, the solution was concentrated to an oil. The title compound, an oil (85 mg, 53%), was isolated by chromatography on silica gel eluting with ethyl acetate.

Workup

  1. washThe organic phase was washed successively with aqueous 1M HCI solution, water, aqueous saturated NaHCO3 solution and brine
  2. dry with materialAfter drying over MgSO4
  3. concentrationthe solution was concentrated to an oil

Sources & evidence

ORD record
ord-c248cf5810a945478cad4f3b71129194
Source dataset
uspto-grants-2002_10
Patent number
US06458822B2

Reaction notes

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