4-Aminobenzyl alcohol → HCID 10731430, compound

HRID 1854668Notes

Reaction equation

HRID 1854668 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10]([NH:17][CH2:18][C:19](O)=[O:20])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:13]([O:12][C:10]([NH:17][CH2:18][C:19]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)=[O:20])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 693314-Aminobenzyl alcoholHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531Diisopropylethylamine

Product 1

HCID 10731430HCID 10731430, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-aminobenzylalcohol (300 mg, 2.43 mmol), N-Boc-glycine (426 mg, 2.43 mmol), and 1-hydroxybenzotriazole (344 mg, 2.55 mmol) in 4.8 mL of dry N,N-dimethylformamide was added N,N-diisopropylethylamine (0.42 mL, 2.9 mmol). After addition of 1-ethyl-3-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochlorde (489 mg, 2.55 mmol) at 0° C., the solution was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and the solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo to obtain crude 4-[2-(tert-butoxycarbonylamino)acetylamino]benzylalcohol.

Workup

  1. washthe solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9094b86fbe164a6cb0d5932c8609ab34
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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