Sodium Azide → Methyl(4S)-5-azido-4-[(tert-butoxy)carbonylamino]pentanoate

HRID 715645Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C>[N:28]([CH2:16][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N+:29]=[N-:30]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-[(4-methylphenyl)sulfonyloxy]pentanoate (4.93 mmol, 1.98 g) was dissolved in DMF (15 mL) and sodium azide (14.8 mmol, 0.961 g) were added. The reaction was heated at 50° C. for 3 hours. The reaction mixture was filtered and the solvent was removed in vacuo. The crude was purified by flash chromatography (SiO2, ethyl acetate) to yield the title compound (1.07 g, 80% yield). ES-MS: 273 (M+1).

Workup

filtrationThe reaction mixture was filtered
customthe solvent was removed in vacuo
customThe crude was purified by flash chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record: ord-a432e4ce11cf44159b374b942e5eb164
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187479B2

Reaction notes

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