1-Hydroxybenzotriazole → HCID 58529717, compound

HRID 1972941Notes

Reaction equation

HRID 1972941 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]([OH:17])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][NH:20][O:21][CH3:22].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>C1COCC1>[CH3:22][O:21][N:20]([CH3:19])[C:15]([CH:13]1[CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:14]1)=[O:17]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

Product 1

HCID 58529717HCID 58529717, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[(benzyloxy)carbonyl]azetidine-3-carboxylic acid (2.30 g, 9.78 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.14 g, 11.73 mmol) in THF (45 mL) was added EDCl (2.06 g, 10.76 mmol), HOBt (1.45 g, 10.76 mmol), N,N-diisopropylethylamine (5.11 mL, 29.33 mmol). The reaction was stirred at rt for 16 h. The mixture was partitioned between ethyl acetate (75 mL) and H2O (75 mL). The layers were separated and the aqueous phase was extracted with ethyl acetate (2 50 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated. The crude material was filtered through a plug of silica gel, eluting with 3:1 ethyl acetate/hexanes to afford 1.66 g (61%) of the desired product after concentration of the filtrate. ES-MS m/z 279.03 [M+H]+, HPLC RT (min) 3.07.

Workup

  1. customThe mixture was partitioned between ethyl acetate (75 mL) and H2O (75 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (2 50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. filtrationThe crude material was filtered through a plug of silica gel
  8. washeluting with 3:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a8f92f1bd79f4db782e69614d1669457
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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