Benzyl chloroformate → HCID 86711811, compound

HRID 1504955Notes

Reaction equation

HRID 1504955 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[CH2:6][CH2:7][CH2:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.[C:16](Cl)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>CN(C=O)C>[CH2:19]([O:18][C:16](=[O:17])[NH:13][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][C:2]2[NH:3][CH2:4][CH2:5][N:1]=2)=[CH:15][CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 68292910HCID 68292910, compound

Product 1

HCID 86711811HCID 86711811, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 55 (318 mg, 1.56 mmol) in DMF (1 mL) was added dropwise CbzCl (0.29 mL, 2.03 mmol) at 0° C. with stirring. The reaction mixture was stirred at room temperature for 3 h. The DMF was removed by vacuum. The residue was purified with silica gel column chromatography (EtOAc:CH3OH:TEA=3:1:0.2) to give compound 56 (400 mg, 76%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ7.70 (s, 1H), 7.30-7.40 (m, 5H), 7.25 (d, 2H, J=8.3 Hz), 6.98 (d, 2H, J=8.3 Hz), 5.15 (s, 2H), 3.65 (s, 4H), 2.50 (t, 2H, J=7.4 Hz), 2.43 (d, 2H, J=7.4 Hz), 1.85-1.97 (m, 2H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 h
  2. customThe DMF was removed by vacuum
  3. customThe residue was purified with silica gel column chromatography (EtOAc:CH3OH:TEA=3:1:0.2)

Sources & evidence

ORD record
ord-4f914ed821a14f61992b5e87a48b3a9c
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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