Methyl 4-aminobenzoate → HCID 50851046, compound

HRID 1271713Notes

Reaction equation

HRID 1271713 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]([NH:19][CH2:20][C:21](O)=[O:22])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:21](=[O:22])[CH2:20][NH:19][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 12082Methyl 4-aminobenzoateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 50851046HCID 50851046, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-amino-benzoate (3.58 g, 23.70 mmol) and N-Boc glycine (4.15 g, 23.70 mmol) were stirred in DMF (50 mL) at room temperature. BOP (11.52 g, 26.07 mmol) was added followed by the addition of DIEA (6.18 mL, 35.55 mmol). The resulting mixture was stirred at rt for 1.5 h. It was quenched with sat'd NaHCO3 and EtOAc. The organic layer was washed with H2O, brine (3×), dried (MgSO4), and concentrated to dryness to give 4-(2-tert-butoxycarbonylamino-acetylamino)-benzoic acid methyl ester (7.18 g, yield: 98%). 1H NMR (CDCl3) δ 9.16 (s, br, 1H), 7.96 (d, J=8.4 Hz, 2H), 7.65 (d, J=8.4 Hz, 2H), 3.98 (s, 2H), 3.89 (s, 3H), 1.45 (s, 9H) ppm.

Workup

  1. customIt was quenched with sat'd NaHCO3 and EtOAc
  2. washThe organic layer was washed with H2O, brine (3×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d16677ec90724422abbeac91823a498d
Source dataset
uspto-grants-2007_04
Patent number
US07205318B2

Reaction notes

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