Pyridine → methanesulfonic acid 2-((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydroindazol-1-yl)-ethyl ester

HRID 1966859Notes

Reaction equation

HRID 1966859 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[NH:10][C@@H:11]1[CH2:19][CH2:18][CH2:17][C:16]2[N:15]([CH2:20][CH2:21][OH:22])[N:14]=[CH:13][C:12]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[CH2:1]([O:8][C:9]([NH:10][C@@H:11]1[CH2:19][CH2:18][CH2:17][C:16]2[N:15]([CH2:20][CH2:21][O:22][S:31]([CH3:30])(=[O:33])=[O:32])[N:14]=[CH:13][C:12]1=2)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59152899(R)-[1-(2-hydroxy-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester

Product 1

HCID 59152906methanesulfonic acid 2-((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydroindazol-1-yl)-ethyl esterYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(R)-1-(2-hydroxy-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester (755 mg, 2.40 mmol) and pyridine (1.45 mL, 18.0 mmol) in dichloromethane was added methanesulfonyl chloride (1.40 mL, 18.0 mmol) dropwise at 0° C. The mixture was warmed to room temperature and stirred for 6 hours. The resulting mixture was poured into ice (10 g). The organic layer was then separated and washed with 0.1 N hydrochloric acid and saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (10% methanol in dichloromethane) to afford methanesulfonic acid 2-((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydroindazol-1-yl)-ethyl ester (880 mg, 90%) as a white solid. MS calcd. for C18H23N3O5S 393, obsd. (ESI+) [(M+H)+] 394.

Workup

  1. customThe organic layer was then separated
  2. washwashed with 0.1 N hydrochloric acid and saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-07cad993057949e8a25343d5b4b010dd
Source dataset
uspto-grants-2013_04
Patent number
US08420675B2

Reaction notes

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