1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 118157845, compound

HRID 1779249Notes

Reaction equation

HRID 1779249 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@H:21]([C@@:39]([OH:51])([CH2:47][C:48]([O-])=[O:49])[C:40]([O:42]C(C)(C)C)=[O:41])/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[Cl-].[NH4+].CC[N:56]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C@:39]([CH2:47][C:48](=[O:49])[NH2:56])([OH:51])[C:40]([OH:42])=[O:41])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 131734862HCID 131734862, compound

Product 1

HCID 118157845HCID 118157845, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

No. 5317776, 1-tert-butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (40.6 mg, 56.9 nmol) was dissolved in DMF (1.0 mL), and ammonium chloride (9.13 mg, 170.6 nmol), WSC (16.4 mg, 85.3 nmol), HOBt (11.5 mg, 85.3 nmol), N,N-diisopropylethylamine (59.4 mL, 341.2 nmol) were added. The mixture was stirred at room temperature for 20 hours. To the reaction solution was added water. The mixture was extracted with ethyl acetate, washed with 1 M hydrochloric acid, an aqueous solution of sodium bicarbonate, and a saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with 1 M hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-4c194afef8ec4bb8b86d9598491ee87a
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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