1-Hydroxybenzotriazole → HCID 86587252, compound

HRID 890584Notes

Reaction equation

HRID 890584 reaction equation
[NH2:1][C@H:2](/[C:29](/[CH3:37])=[CH:30]/[C:31]1[N:32]=[C:33]([CH3:36])[S:34][CH:35]=1)[CH2:3][C@@H:4]1[O:28][C@:5]1([CH3:27])[CH2:6][CH2:7][C:8](=[O:26])[C@H:9]([CH3:25])[C@H:10]([OH:24])[C@@H:11]([CH3:23])[C:12](=[O:22])[C:13]([CH3:21])([CH3:20])[C@@H:14]([OH:19])[CH2:15][C:16]([OH:18])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(#N)C.CN(C)C=O.O>[O:28]1[C@@H:4]2[C@@:5]1([CH3:27])[CH:6]=[CH:7][C:8](=[O:26])[C@H:9]([CH3:25])[C@H:10]([OH:24])[C@@H:11]([CH3:23])[C:12](=[O:22])[C:13]([CH3:21])([CH3:20])[C@@H:14]([OH:19])[CH2:15][C:16](=[O:18])[NH:1][C@H:2]([C:29]([CH3:37])=[CH:30][C:31]1[N:32]=[C:33]([CH3:36])[S:34][CH:35]=1)[CH2:3]2

Participants

6

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59645497HCID 59645497, compound

Product 1

HCID 86587252HCID 86587252, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

A solution of (3S,6R,7S,8R,12R,13S,15S,16E)-15-amino-3,7-dihydroxy-5,9-dioxo-12,13-epoxy-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-16-heptadecenoic acid (540 mg) in acetonitrile/dimethylformamide (20:1 v/v, 150 mL) is cooled to 0° C. and treated sequentially with 1-hydroxybenzotriazole (0.135 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.5 g). The mixture is warmed to ambient temperature and kept for 12 hours, then diluted with water and extracted with ethyl acetate. The extract is washed sequentially with water, sat. NaHCO3, and brine, then dried over Na2SO4, filtered, and evaporated. The product is purified by flash chromatography on SiO2.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed sequentially with water, sat. NaHCO3, and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe product is purified by flash chromatography on SiO2

Sources & evidence

ORD record
ord-5a7901b0b71a4725ae1495578e7235f8
Source dataset
uspto-grants-2006_02
Patent number
US06998256B2

Reaction notes

Loading…