1-(Chloromethoxy)-2-methoxyethane → HCID 22942184, compound

HRID 361962Notes

Reaction equation

HRID 361962 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:25])[C@H:6]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[CH3:26][O:27][CH2:28][CH2:29][O:30][CH2:31]Cl.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:26][O:27][CH2:28][CH2:29][O:30][CH2:31][O:1][CH2:2][CH2:3][NH:4][C:5](=[O:25])[C@H:6]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 14036746HCID 14036746, compound

Product 1

HCID 22942184HCID 22942184, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-phenylalanine-N-(2-hydroxylethyl)amide (7.0 g, 20.4 mmol) in dry dichloromethane (150 ml) under an argon atmosphere was added 2-methoxyethoxymethyl chloride (5.6 ml, 49.0 mmol) and diisopropylethylamine (10.7 ml, 61.4 mmol). The reaction mixture was stirred overnight at room temperature, after which time starting material was still detectable by TLC. The solvent volume was concentrated to one third, an equal volume of DMF was added and the reaction mixture was stirred for a further 60 hours at room temperature. The solvents were removed under reduced pressure, the residue was dissolved in ethyl acetateand washed successively with 1M hydrochloric acid, sat. aq. sodium hydrogencarbonate and brine. The organic phase was dried over sodium sulphate, filtered and concentrated to afford the desired product as a pale yellow oil which crystallised when left under high vacuum for ca. 1 hour. Yield: 8.0 g (90%). 1H--NMR; δ(CDCI3), 7.33-7.14 (10H, m), 6.84 (1H, br s), 5.89 (1H, br s), 5.01 (2H, m), 4.54 (2H, s), 4.46 (1H, m), 3.56-3.26 (11H, m), 3.02 (2H, m).

Workup

  1. concentrationThe solvent volume was concentrated to one third
  2. additionan equal volume of DMF was added
  3. stirringthe reaction mixture was stirred for a further 60 hours at room temperature
  4. customThe solvents were removed under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl
  6. washwashed successively with 1M hydrochloric acid, sat. aq. sodium hydrogencarbonate and brine
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a1295345bbc6415db17441362b24c830
Source dataset
uspto-grants-1999_02
Patent number
US05866717

Reaction notes

Loading…