Dicyclohexylcarbodiimide → Methyl 2,2,5-trimethyl-4-oxo-3,6,9-trioxa-5-azaundecan-11-yl adipate

HRID 1529835Notes

Reaction equation

HRID 1529835 reaction equation
OC[CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[C:18]([O:27][CH3:28])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O-:25])=[O:24].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:18]([O:27][CH3:28])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:24]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 6994472Methyl adipateHCID 86628343Tert-butyl 2-(3-hydroxypropoxy)ethoxy(methyl)carbamate

Product 1

HCID 86628344Methyl 2,2,5-trimethyl-4-oxo-3,6,9-trioxa-5-azaundecan-11-yl adipate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(3-hydroxypropoxy)ethoxy(methyl)carbamate (152 mg, 0.646 mmol) and monomethyl adipate (104 mg, 0.646 mmol) in CH2Cl2 (4 mL) were added DCC (146 mg, 0.711 mmol) and DMAP (16 mg, 0.129 mmol). The reaction mixture was stirred at room temperature for 16 h and filtered. The solvent was removed under reduced pressure. The crude product was purified by silica gel flash column chromatography using 27% EtOAc/hexanes as eluent. The desired product was obtained as colorless oil (152 mg, 0.403 mmol, 62%). 1H NMR (CDCl3, 400 MHz): 6 (ppm) 1.41 (s, 9H), 1.56-1.60 (m, 4H), 2.25-2.27 (m, 4H), 3.03 (s, 3H), 3.58 (s, 3H), 3.59-3.63 (m, 4H), 3.91-3.94 (m, 2H), 4.14-4.16 (m, 2H).

Workup

  1. filtrationfiltered
  2. customThe solvent was removed under reduced pressure
  3. customThe crude product was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-83e94251a1cb4b90ba0ae543afa21168
Source dataset
uspto-grants-2015_07
Patent number
US09090643B2

Reaction notes

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