1-Iodohexadecane → HCID 54361281, compound

HRID 1384761Notes

Reaction equation

CCN(C(C)C)C(C)C.I[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[CH3:27][C@@H:28]([C:31]([N:33]1[C@H:37]([C:38]([OH:40])=[O:39])[CH2:36][CH2:35][CH2:34]1)=[O:32])[CH2:29][SH:30].C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH2:11]([S:30][CH2:29][C@@H:28]([CH3:27])[C:31]([N:33]1[CH2:34][CH2:35][CH2:36][C@H:37]1[C:38]([OH:40])=[O:39])=[O:32])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 70 °C

Procedure

DIEA (188 μl, 1.10 mmol) was added to a solution of 1-iodohexadecane (176 mg, 0.500 mmol), captopril (120 mg, 0.550 mmol) and DBU (165 μl, 1.10 mmol) in tetrahydrofuran (5 ml). The mixture was heated at 70° C. for 2 hours and then concentrated. The residue was poured onto water saturated with potassium hydrogen sulphate and organic material was extracted into chloroform. The organic phase was washed with water and dried (MgSO4). The product was purified by chromatography (silica, CHCl3/MeOH/AcOH 85:10:5) and lyophilised to give 105 mg (48%) of white solid material. The structure was verified by 1H (500 Mhz) and 13C (125 Mhz) NMR analysis and further characterised by MALDI mass spectrometry, giving M-H in negative mode at m/z 440 as expected.

Workup

concentrationconcentrated
additionThe residue was poured onto water saturated with potassium hydrogen sulphate and organic material
extractionwas extracted into chloroform
washThe organic phase was washed with water
dry with materialdried (MgSO4)
customThe product was purified by chromatography (silica, CHCl3/MeOH/AcOH 85:10:5)

Sources & evidence

ORD record: ord-56a0e4adfeca4c22990424bd3b43d757
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06261537B1

Reaction notes

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