1-Hydroxybenzotriazole → HCID 22884119, compound

HRID 1598451Notes

Reaction equation

HRID 1598451 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])([O:3]C(C)(C)C)=O.[CH2:17]([NH:24][CH2:25]C(OCC)=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[CH2:17]([N:24]1[CH2:25][C:1](=[O:3])[NH:8][C@@H:9]([CH2:10][CH2:11][S:12][CH3:13])[C:14]1=[O:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 80908N-Benzylglycine ethyl esterHCID 89857Boc-L-methionineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22884119HCID 22884119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

The title compound was prepared according to the procedure described in Example 2, Step A, except using Boc-L-methionine (10.0 g, 40.0 mmol), ethyl N-benzylglycinate (7.75 g, 40.0 mmol), HOBT (5.41 g, 40.0 mmol) and EDC.HCl (7.68 g, 40.00 mmol) in dimethylformamide. Upon completion of the reaction, the dimethylformamide was removed in vacuo and the crude product partitioned between ethyl acetate and water. The organic phase was washed with water and saturated sodium chloride solution, then dried over sodium sulfate. The solvent was removed in vacuo and the residue taken up in methylene chloride (200 mL). Trifluoroacetic acid (100 mL) was added and the reaction stirred at 20° C. for 2 h. The volatiles were removed in vacuo and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. The title compound was obtained as a white solid (9.08 g). NMR (CHCl3, 300 MHz) δ 7.4-7.2 (6H, m); 4.60 (2H, AB q, J=13 Hz); 4.24 (1H, m); 3.85 (2H, AB q, J=18 Hz); 2.63 (2H, t, J=7Hz); 2.3-2.1 (2H, m); 2.1 (3H, s).

Workup

  1. customThe title compound was prepared
  2. customUpon completion of the reaction
  3. customthe dimethylformamide was removed in vacuo
  4. customthe crude product partitioned between ethyl acetate and water
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo
  8. additionTrifluoroacetic acid (100 mL) was added
  9. customThe volatiles were removed in vacuo
  10. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  11. washThe organic phase was washed with saturated sodium chloride solution
  12. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-1862ebc9cedc4baf98463803e7a9cebc
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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