Triethylene glycol monomethyl ether → HCID 131732578, compound

HRID 874847Notes

Reaction equation

HRID 874847 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9](=[O:20])[C@H:10]([CH3:19])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26]COCCO.C(N[C@H](C(O)=O)C)(OC(C)(C)C)=O.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl.CO>[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9](=[O:20])[C@H:10]([CH3:19])[NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13]

Participants

7

Reactant 4

HCID 8178Triethylene glycol monomethyl etherHCID 10868DicyclohexylcarbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 123807908HCID 123807908, compound

Product 1

HCID 131732578HCID 131732578, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Compound 2b was prepared using the same procedure as described for the synthesis of 2a with the following reactants and solvents: 2-(2-(2-methoxyethoxy)ethoxy)ethanol (1.32 g, 8 mmol), 4-N,N′-(dimethyl)aminopyridine (100 mg, 0.81 mmol), N-Boc-(L)-Alanine (1.51 g, 8 mmol) and DCC (1.67 g, 8.1 mmol) in dichloromethane (25 mL). Column chromatography (SiO2, 0.060-0.200 mm/1% MeOH in CH2Cl2) yielded compound 2b as a colorless to pale yellow oil (2.35 g, 7.1 mmol, 86%).

Workup

  1. customCompound 2b was prepared

Sources & evidence

ORD record
ord-5f74c731f0bc45de8a1eafb372ec37c3
Source dataset
uspto-grants-2015_03
Patent number
US08981001B2

Reaction notes

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