Diisopropylethylamine → HCID 68166311, compound

HRID 2175251Notes

Reaction equation

HRID 2175251 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].CCN(C(C)C)C(C)C.[C:17](Cl)(=[O:28])[O:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][C:17]([NH:2][CH2:3][C:4]([O:6][CH3:7])=[O:5])=[O:28])=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 68166311HCID 68166311, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2-aminoacetate hydrochloride (0.137 g, 1.09 mmol) and DIPEA (0.52 mL, 2.98 mmol) in DCM (5 mL) at 0° C. was added a solution of 4-nitrophenyl carbonochloridate (0.20 g, 0.992 mmol) in DCM (2 mL) dropwise. The reaction mixture was slowly warmed to room temperature and stirred for 16 h. After this time, the reaction was quenched with water, and the organic layer was separated. The aqueous phase was extracted with DCM, and the combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (0.213 g, 84% yield) as a white solid. LCMS, [M+Na]+=277.1. 1H NMR (400 MHz, CDCl3) δ 8.24 (d, J=9.1 Hz, 2H), 7.32 (d, J=9.1 Hz, 2H), 5.62 (br. s, 1H), 4.07 (d, J=5.5 Hz, 2H), 3.80 (s, 3H).

Workup

  1. customAfter this time, the reaction was quenched with water
  2. customthe organic layer was separated
  3. extractionThe aqueous phase was extracted with DCM
  4. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide the crude material
  8. customThe crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-f41d55a83baf43bd832386a9e1f3a359
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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