Triethylamine → Methyl 7-(2-trimethylsilanyl-ethoxycarbonylamino)-heptanoate

HRID 1779225Notes

Reaction equation

HRID 1779225 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH3:13][Si:14]([CH3:29])([CH3:28])[CH2:15][CH2:16][O:17][C:18](ON1C(=O)CCC1=O)=[O:19].C(N(CC)CC)C>ClCCl>[CH3:13][Si:14]([CH3:29])([CH3:28])[CH2:15][CH2:16][O:17][C:18]([NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 13807349Methyl 7-aminoheptanoate hydrochloride

Product 1

HCID 123550597Methyl 7-(2-trimethylsilanyl-ethoxycarbonylamino)-heptanoateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 7-amino-heptanoate hydrochloride (7.0 g, 35.9 mmol) was dissolved in dichloromethane (75.4 mL), and N-[2-(trimethylsilyl)ethoxycarbonyloxy]succinimide (10.0 g, 38.6 mmol) and triethylamine (10 mL, 71.7 mmol) were then added at room temperature. The mixture was stirred for 5 hours, and then quenched with water (100 mL), and separated. The aqueous layer was extracted with dichloromethane (50 mL). The organic layers were combined, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure to obtain 8.89 g (29.3 mmol, 82% yield) of methyl 7-(2-trimethylsilanyl-ethoxycarbonylamino)-heptanoate.

Workup

  1. customquenched with water (100 mL)
  2. customseparated
  3. extractionThe aqueous layer was extracted with dichloromethane (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-25bf88dcafd64583b118ebc99c3c8356
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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