Water → HCID 56978808, compound

HRID 492660Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To E5 (1.528 g, 2.693 mmol) in anhydrous DMF (70 ml) was added sodium azide (1.226 g, 18.851 mmol) and the reaction heated for 5 days at 50° C. under argon. The solvent was reduced to almost dryness and the residues taken up into water (150 ml) and ethyl acetate (150 ml). The aqueous layer was further extracted with ethyl acetate (4×150 ml), the fractions combined, washed (2×150 ml water), dried (MgSO4) and the solvent removed to quantitatively yield the title compound as a pale yellow waxy solid 1.465 g, 95%. C36H67O2N3 requires 573.5. Found ES−: (M−H+)−, 572.6. dH (CDCl3) 1.27 (46H, br, N3(CH2)2(CH2)8 CH2CH═CHCH2(CH2)8CH2CH═CHCH2 (CH2)7), 1.63 (4H, m, CH2CH2N3), CH2H2CO2H), 2.02 (8H, m, CH2CH═), 2.34 (2H, t, CH2CO). 3.35 (2H, t, CH2N3), 5.35 (4H, m, CH═CH).

Workup

extractionThe aqueous layer was further extracted with ethyl acetate (4×150 ml)
washwashed (2×150 ml water)
dry with materialdried (MgSO4)
customthe solvent removed

Sources & evidence

ORD record: ord-57490329c6d44d7aa1a70934772ba6a9
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531676B2

Reaction notes

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