1,2-Dichloroethane → HCID 66936469, compound

HRID 1366424Notes

Reaction equation

HRID 1366424 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][C@@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:18][O:19][C:20](=[O:24])[CH2:21][NH:22][CH3:23].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9]([NH:11][C@@H:12]([C:14]([N:22]([CH3:23])[CH2:21][C:20]([O:19][CH3:18])=[O:24])=[O:16])[CH3:13])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 70832N-Cbz-d-alanineHCID 757711-HydroxybenzotriazoleHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)

Product 1

HCID 66936469HCID 66936469, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-{[(phenylmethyl)oxy]carbonyl}-D-alanine (133.53 g, 598.2 mmol) in DCM (1100 mL) was added powdered sarcosine methyl ester hydrochloride (83.49 g, 598.2 mmol), 1-hydroxybenzotriazole (80.81 g, 598.1 mmol), and 4-methylmorpholine (242 mL, 2201 mmol). The mixture was stirred for 10 min, and then EDC (114.68 g, 598.2 mmol) was added. The mixture was stirred overnight, and was then washed with water (500 mL), 1 N aqueous HCl (2×300 mL), and brine (300 mL). The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude methyl N-{[(phenylmethyl)oxy]carbonyl}-D-alanyl-N-methylglycinate (162.35 g, 88% yield) as a yellow oil. LCMS: (M+H)+: 309.0.

Workup

  1. stirringThe mixture was stirred overnight
  2. washwas then washed with water (500 mL), 1 N aqueous HCl (2×300 mL), and brine (300 mL)
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e675cdbf85d642189722e0702588b61b
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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