4-Methylmorpholine → Tert-butyl 2-(4-(benzyloxy)-3-tert-butylbenzamido)acetate

HRID 2225266Notes

Reaction equation

HRID 2225266 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[C:18]([CH3:21])([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][C:27](=[O:30])[CH2:28][NH2:29])([CH3:25])([CH3:24])[CH3:23].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CCOC(C)=O.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:29][CH2:28][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:30])=[O:15])=[CH:11][C:10]=1[C:18]([CH3:21])([CH3:20])[CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 151417Glycine tert-butyl esterHCID 19029807HCID 19029807, compound

Product 1

HCID 69285477Tert-butyl 2-(4-(benzyloxy)-3-tert-butylbenzamido)acetateYield 102%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(benzyloxy)-3-tert-butylbenzoic acid (2.36 g, 8.31 mmol) in anhyd DMF (56 mL) was added glycine t-butyl ester (1.63 g, 12.5 mmol), BOP reagent (5.51 g, 12.5 mmol), and N-methylmorpholine (2.74 mL, 24.9 mmol). The mixture was stirred at room temperature for 12 h under nitrogen atmosphere and then diluted with EtOAc (200 mL). The organic layer was washed consecutively with 1 N HCl (250 mL), satd NaHCO3 (100 mL), 5% LiCl (2×100 mL), and brine (50 mL), dried (Na2SO4), and concentrated in vacuo. tert-butyl 2-(4-(benzyloxy)-3-tert-butylbenzamido)acetate (3.37 g, quant.) was isolated as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.81 (s, 1H), 7.63-7.60 (m, 1H), 7.46-7.34 (m, 5H), 6.95-6.93 (m, 1H), 6.52 (s, 1H), 5.16 (s, 2H), 4.14-4.11 (m, 2H), 1.51 (s, 9H), 1.41 (s, 9H); MS found: (M+H)+=398.

Workup

  1. washThe organic layer was washed consecutively with 1 N HCl (250 mL), satd NaHCO3 (100 mL), 5% LiCl (2×100 mL), and brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a40cdad7cbd442109dee5c996ee706e1
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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