HCID 11267230, compound → HCID 86741165, compound

HRID 1249296Notes

Reaction equation

[N+:1]([C:4]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[N+:14]=[N-:15])=[CH:9][CH:8]=1)([O-:3])=[O:2].[N+:23]([C:26]1[CH:45]=[CH:44][C:29]([CH2:30][O:31][C:32](=[O:43])[C:33](=[CH2:42])[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:28][CH:27]=1)([O-:25])=[O:24]>C(Cl)Cl>[C:38]([O:37][C:35]([NH:34][C:33]1([C:32]([O:31][CH2:30][C:29]2[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:45][CH:44]=2)=[O:43])[CH2:42][CH:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][C:5]3[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:4]=3[N+:1]([O-:3])=[O:2])=[CH:8][CH:9]=2)[NH:14][NH:15]1)=[O:36])([CH3:39])([CH3:40])[CH3:41]

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of 4-(2,4-dinitrophenoxy)-phenyldiazomethane in CH2Cl2 (20 ml) is added to a solution of Boc-dehydroalanine-p-nitrobenzyl ester (2) in 20 ml CH2Cl2 at -15° C. After stirring 1 hr at -15° C. and 4 hr at 25°, the solution is evaporated to dryness and the residue is triturated with hexane. The solid product, p-nitrobenzyl 3-t-butoxycarbonylamino-5-(4-[2,4-dinitrophenoxyl]-phenyl)-pyrazoline-3-carboxylate (18), is recrystallized from ethyl acetate-hexane to constant melting point. NMR (CDCl3)δ: 4.8-5.4 (m, 1H, CH--N=N).

Workup

customthe solution is evaporated to dryness
customthe residue is triturated with hexane
customThe solid product, p-nitrobenzyl 3-t-butoxycarbonylamino-5-(4-[2,4-dinitrophenoxyl]-phenyl)-pyrazoline-3-carboxylate (18), is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-e36b45eb28e7494ba39d85e2af9d798d
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04629784

Reaction notes

Loading…