Triethylamine → HCID 131736535, compound

HRID 1478981Notes

Reaction equation

HRID 1478981 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH3:6][O:7][CH:8]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:9][CH:10]([O:14][C:15]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]([NH2:13])=[O:12].[OH:44]CCCCCCCCCCCC(O)=O.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl.N1C=CC=CC=1>[OH:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:8][CH2:9][CH2:10][C:11]([NH:13][NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:12].[CH3:6][O:7][CH:8]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:9][CH:10]([O:14][C:15]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]([NH2:13])=[O:12]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 7903412-Hydroxydodecanoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 131736538HCID 131736538, compound

Product 1

HCID 131736535HCID 131736535, compoundYield 131.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

Compound 4 (3.15 g, 5.62 mmol) was dried three times by azeotropic distillation with anhydrous pyridine, 12-hydroxydodecanoic acid (3.41 g, 6.74 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.29 g, 6.74 mmol), 1-hydroxybenzotriazole monohydrate (2.06 g, 13.48 mmol) and anhydrous dichloromethane (50 ml) were added at room temperature under an argon atmosphere, and the mixture was stirred for 10 min. To the thus-obtained mixture was added triethylamine (2.05 g, 20.22 mmol), and the mixture was stirred at room temperature overnight under an argon atmosphere. To the obtained reaction mixture was added dichloromethane (200 ml), and the mixture was washed three times with saturated aqueous sodium hydrogen carbonate, and further washed once with saturated brine. The organic layer was fractionated, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: dichloromethane-methanol (95:5)+0.05% pyridine) to give hydroxydodecanamidoglycine-4,4′-dimethoxytrityloxydodecanamide (5) (2.97 g, 70%) as a colorless syrup. The instrumental analysis values of hydroxydodecanamidoglycine-4,4′-dimethoxytrityloxydodecanamide (5) are shown below.

Workup

  1. additionwere added at room temperature under an argon atmosphere
  2. stirringthe mixture was stirred at room temperature overnight under an argon atmosphere
  3. customTo the obtained reaction mixture
  4. washthe mixture was washed three times with saturated aqueous sodium hydrogen carbonate
  5. washfurther washed once with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluent: dichloromethane-methanol (95:5)+0.05% pyridine)

Sources & evidence

ORD record
ord-e573890be02b41b7bcdf38eb8d53a303
Source dataset
uspto-grants-2016_08
Patent number
US09404108B2

Reaction notes

Loading…