Sodium Azide → HCID 117871264, compound

HRID 525297Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH3:41])[C@@H:9]([CH3:40])[C:10]([NH:12][C@@H:13]([CH:37]([CH3:39])[CH3:38])[C:14]([N:16]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH2:18][C@H:17]1[CH2:25]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:42]=[N+:43]=[N-:44].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([C@H:9]([C:10](=[O:11])[NH:12][C@H:13]([C:14]([N:16]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH2:18][C@H:17]1[CH2:25][N:42]=[N+:43]=[N-:44])=[O:15])[CH:37]([CH3:39])[CH3:38])[CH3:40])[CH3:41])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of toluene-4-sulfonic acid (S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-2-ylmethyl ester (Intermediate 2) (200 mg, 0.34 mmol) in DMF (4 mL) was added NaN3 (26.53 mg, 0.408 mmol) and the resulting mixture was heated at 90° C. for 3 h. The reaction was concentrated in vacuo and the obtained residue was dissolved in ethyl acetate (25 mL) and washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by flash chromatography (silica gel, 12% EtOAc in hexanes) to give {(S)-1-[(S)-1-((S)-2-azidomethyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (140 mg), m/z=460 (M+H).

Workup

concentrationThe reaction was concentrated in vacuo
dissolutionthe obtained residue was dissolved in ethyl acetate (25 mL)
washwashed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting residue was purified by flash chromatography (silica gel, 12% EtOAc in hexanes)

Sources & evidence

ORD record: ord-e373d98605894a5fb0b46180a47810c1
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340573B2

Reaction notes

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