Benzylamine → HCID 59923944, compound

HRID 2298566Notes

Reaction equation

HRID 2298566 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C@H:10]([CH2:25][CH2:26][CH3:27])[C@H:11]([CH3:24])[C:12](N1C2C=CC=CC=2OC1=O)=[O:13]>O1CCCC1>[CH2:1]([NH:8][C:12](=[O:13])[C@@H:11]([CH3:24])[C@H:10]([OH:9])[CH2:25][CH2:26][CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 69464704HCID 69464704, compound

Product 1

HCID 59923944HCID 59923944, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzylamine (0.6 mL, 5.5 mmol) is added dropwise to a solution of N-[(2S*,3R*)-3-hydroxy-2-methylhexanoyl]-2-benzoxazolinone (1.31 g, 5.0 mmol) in 10 mL of tetrahydrofuran. A mildly exothermic reaction ensues. After 15 min, the solvent is evaporated. The residue is redissolved in 50 mL of CH2Cl2 and washed successively with equal volumes of 1 N HCl, 1 N NaOH, water, and brine. After drying over MgSO4, the solution is evaporated to yield 1.12 g (95% yield) of the product as a white solid which was recrystallized from ethyl acetate/hexanes as white needles, mp 114-115° C. 1H-NMR (d6-DMSO, 400 MHz) δ 8.27 (t, J=6, 1H), 7.30 (m, 2H), 7.22 (m, 3H), 4.49 (d, J=6, 1H), 4.27 (dd, J=6, 15, 1H), 4.20 (dd, J=6,15, 1H), 3.44 (m, 1H), 2.20 (q, J=7, 1H), 1.43 (m, 1H), 1.22 (m, 3H), 1.04 (d, J=7, 3H), 0.79 (t, J=7, 3H). 13C-NMR (d6-DMSO, 100 MHz): 175.2, 140.2, 128.6, 127.6, 127.1, 71.8, 46.9, 42.2, 37.6, 19.0, 14.7, 14.5.

Workup

  1. customA mildly exothermic reaction
  2. customthe solvent is evaporated
  3. dissolutionThe residue is redissolved in 50 mL of CH2Cl2
  4. washwashed successively with equal volumes of 1 N HCl, 1 N NaOH, water, and brine
  5. dry with materialAfter drying over MgSO4
  6. customthe solution is evaporated

Sources & evidence

ORD record
ord-1ada91f4833043cfbe8e85b03c026594
Source dataset
uspto-grants-2002_12
Patent number
US06492562B1

Reaction notes

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