1-Hydroxybenzotriazole → HCID 86650707, compound

HRID 1873692Notes

Reaction equation

HRID 1873692 reaction equation
Cl.[F:2][C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[C:8]([NH:15][CH2:16][C:17](O)=[O:18])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O1CCCC1.C(N(CC)CC)C>[F:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:17](=[O:18])[CH2:16][NH:15][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:4]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16217739(s)-3-Fluoropyrrolidine hydrochloride

Product 1

HCID 86650707HCID 86650707, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

(S)-3-Fluoropyrrolidine hydrochloride (535 mg), N-Boc glycine (746 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.41 g), 1-hydroxybenzotriazole (993 mg), and triethylamine (1.19 mL) were dissolved in tetrahydrofuran (5 mL), and the solution was stirred at 70° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and aqueous saturated sodium bicarbonate (20 mL) was added to the residue, followed by extraction with ethyl acetate (10 mL). The organic layer was washed sequentially with 0.1N HCl (10 mL) and saturated brine (10 mL) and dried over sodium sulfate, followed by concentration under reduced pressure, to thereby yield compound 20a (98.1 mg, yield: 9.3%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and aqueous saturated sodium bicarbonate (20 mL)
  2. additionwas added to the residue
  3. extractionfollowed by extraction with ethyl acetate (10 mL)
  4. washThe organic layer was washed sequentially with 0.1N HCl (10 mL) and saturated brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-6f72a3539bac46bbb0930b59828b8637
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

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