N-(tert-butoxycarbonyl)glycine → HCID 21904412, compound

HRID 2190702Notes

Reaction equation

HRID 2190702 reaction equation
[C:1]([NH:8]CC(O)=O)([O:3][C:4]([CH3:7])(C)C)=[O:2].Br[C:14]1[CH:23]=[CH:22][C:17](CCCN)=[CH:16][CH:15]=1.CCN(C(C)C)C(C)C.C([O-])(O)=[O:34].[Na+]>C(Cl)Cl.O>[CH3:7][CH2:4][O:3][C:1]([CH3:14])=[O:2].[CH3:22][CH2:23][CH2:14][CH2:15][CH2:16][CH3:17].[NH4+:8].[OH-:34]

Participants

7

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 12376816HCID 12376816, compound

Product 1

HCID 21904412HCID 21904412, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-glycine 130 (1.04 g, 5.88 mmol) and 4-bromobenzylethylamine 131 (1.00 g, 4.90 mmol) in CH2Cl2 (25 mL) at room temperature was added Hunig's base (1.30 mL, 7.35 mmol). The mixture was stirred at room temperature for 16 h. The mixture was poured into water (40 mL) and sat. NaHCO3 (3 mL), then extracted with CH2Cl2 (60 mL), washed with water (100 mL), and dried with Na2SO4. The residue was isolated by column chromatography (50/50/0.1 EtOAc/Hexane/NH4OH), to give 1.30 g of amide 132 as a white crystalline solid in 69% yield. 1H NMR (300 MHz, CDCl3, ppm): δ: 7.37 (d, J=7 Hz, 2H), 7.09 (d, J=7 Hz, 1H), 6.50 (s br, 1H), 5.15 (s br, 1H), 5.01-4.95 (m, 1H), 3.69 (d, J=6 Hz, 2H), 1.39 (d, J=7 Hz, 3H), 1.37 (s, 9H).

Workup

  1. extractionextracted with CH2Cl2 (60 mL)
  2. washwashed with water (100 mL)
  3. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-fa709816834c450b95ce0487cfa321e5
Source dataset
uspto-grants-2012_12
Patent number
US08324398B2

Reaction notes

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