Triethylamine → 4-Benzyloxy-1-butyloxycarbonylamino-3-nitrobenzene

HRID 260649Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:3].[N+:9]([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C(O)=O)([O-:11])=[O:10].C([N:31](CC)CC)C.[N-]=[N+]=[N-].[Na+]>CC(C)=O.O>[CH2:22]([O:21][C:20]1[CH:19]=[CH:18][C:14]([NH:31][C:2]([O:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:3])=[CH:13][C:12]=1[N+:9]([O-:11])=[O:10])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: -5 °C

Procedure

12.4 ml (93.6 mmol) of butyl chloroformate in 80 ml of acetone are added to a solution of 24.3 g of 3-nitro4-benzyloxybenzoic acid (J. Med. Chem. 1967 (10) 462) and 8.7 g (86.4 mmol) of triethylamine in 200 ml of acetone at 0° C. The mixture was stirred at -5° C. for a further hour, 7.0 g (108 mmol) of sodium azide in 100 ml of water are then added dropwise and the mixture is stirred at 0° C. for 2 hours. The mixture is subsequently introduced onto 800 ml of ice-water and the precipitate which has separated out is filtered off with suction and then introduced into 300 ml of boiling n-butanol.

Workup

stirringthe mixture is stirred at 0° C. for 2 hours
customthe precipitate which has separated out
filtrationis filtered off with suction
additionintroduced into 300 ml of boiling n-butanol

Sources & evidence

ORD record: ord-0af8b939fe534b969ffa956aa621ba5f
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05529998

Reaction notes

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