Dicyclohexylcarbodiimide → HCID 23039619, compound

HRID 2166433Notes

Reaction equation

[CH2:1]([O:17][CH2:18][C:19](=[CH2:22])[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1(N=C=NC2CCCCC2)CCCCC1.[Br:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](O)=[O:45]>CCOCC.CN(C)C1C=CN=CC=1>[CH2:1]([O:17][CH2:18][C:19](=[CH2:22])[CH2:20][O:21][C:44](=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][Br:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 22 °C

Procedure

3-Hexadecyloxy-2-methylenepropan-1-ol (from Preparation 1) (1.8 g) was dissolved in ether (35 ml). Dicyclohexylcarbodiimide (1.5 g), 4-dimethylaminopyridine (0.07 g) and 6-bromohexanoic acid (1.2 g) was added, and the mixture was stirred at 22° C. for 18 hours. The reaction mixture was filtered, and the filtrate was washed with water (35 ml), 5% acetic acid in water (35 ml) and water (35 ml). The ether solution was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The crude product was purified by chromatography on a Waters PrepLC®/System 500A using a PrepPAK®-500/SILICA cartridge first with ether/pentane 1:4 and in a second run with methylene chloride/hexane 1:4 as eluent.

Workup

filtrationThe reaction mixture was filtered
washthe filtrate was washed with water (35 ml), 5% acetic acid in water (35 ml) and water (35 ml)
dry with materialThe ether solution was dried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated in vacuo
customThe crude product was purified by chromatography on a Waters PrepLC®/System 500A

Sources & evidence

ORD record: ord-c2e322d8dcb34c57a6796c9bca40068b
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04945098

Reaction notes

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