Methanol → HCID 123807908, compound

HRID 874846Notes

Reaction equation

HRID 874846 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[C:9]([NH:16][C@H:17]([C:19](O)=[O:20])[CH3:18])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1(N=C=NC2CCCCC2)CCCCC1.CO>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:19](=[O:20])[C@H:17]([CH3:18])[NH:16][C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 8134Diethylene Glycol Monomethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 123807908HCID 123807908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(2-Methoxyethoxy)ethanol (1.28 g, 10.5 mmol), 4-N,N′-(dimethyl)aminopyridine (128 mg, 1 mmol) and N-Boc-(L)-alanine (2 g, 10.5 mmol) were dissolved in freshly distilled CH2Cl2 (25 mL). The reaction mixture was cooled to 0° C. (ice bath) and dicyclohexylcarbodiimide (DCC, 2.39 g, 1.1 mmol) was added portionwise. The reaction mixture was stirred for 1 h at 0° C. and then warmed up to room temperature over 2 h. The dicyclohexyl urea was filtered off, washed with ethyl acetate (2×20 mL) and the solvents evaporated. Column chromatography (SiO2, 0.060-0.200 mm/1% MeOH in CH2Cl2) yielded compound 2a as a colorless to pale yellow oil (2.40 g, 8.3 mmol, 79%).

Workup

  1. additionwas added portionwise
  2. temperaturewarmed up to room temperature over 2 h
  3. filtrationThe dicyclohexyl urea was filtered off
  4. washwashed with ethyl acetate (2×20 mL)
  5. customthe solvents evaporated

Sources & evidence

ORD record
ord-56a0d82b84d342548567e9b0b54189ca
Source dataset
uspto-grants-2015_03
Patent number
US08981001B2

Reaction notes

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