Water → 3-{2-(2-Amino-ethyl)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid methyl ester

HRID 1181086Notes

Reaction equation

HRID 1181086 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH2:27][CH2:28][NH:29]C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH2:27][CH2:28][NH2:29]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 589795263-{2-(2-tert-Butoxycarbonylamino-ethyl)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid methyl ester

Product 1

HCID 589790753-{2-(2-Amino-ethyl)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid methyl esterYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{2-(2-tert-butoxycarbonylamino-ethyl)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid methyl ester (0.90 g, 1.77 mmol) in CH2Cl2 (10 mL) at 0° C. was treated with TFA (5.0 mL) and water (0.2 mL). The resulting solution was allowed to warm gradually to ambient temperature. After 18 h, the mixture was concentrated. The residue was partitioned between CH2Cl2 (30 mL) and 5N NaOH (2 mL), and the aqueous layer was extracted with CH2Cl2 (3×30 mL). The combined organics were dried (K2CO3) and concentrated to a residue, which was purified by silica gel chromatography (CH2Cl2/MeOH/NH4OH, 8/2/0.05) to afford the title compound as a colorless oil (0.42 g, 58%). 1H NMR (400 MHz, CDCl3): δ 2.34 (s, 3H), 2.52 (t, 2H, J=7.8 Hz), 2.81 (t, 2H, J=7.8 Hz), 2.91 (t, 4H, J=6.4 Hz), 3.06 (t, 2H, J=7.3 Hz), 3.60 (s, 3H), 4.20 (t, 2H, J=6.8 Hz), 6.68 (br s, 1H), 6.71 (d, 1H, J=8.3 Hz), 7.01 (d, 1H, J=8.3 Hz), 7.37-7.39 (m, 3H), 7.89-7.92 (m, 2H).

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was partitioned between CH2Cl2 (30 mL) and 5N NaOH (2 mL)
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×30 mL)
  4. dry with materialThe combined organics were dried (K2CO3)
  5. concentrationconcentrated to a residue, which
  6. customwas purified by silica gel chromatography (CH2Cl2/MeOH/NH4OH, 8/2/0.05)

Sources & evidence

ORD record
ord-2f7980b4437c47f09c3a33a7c8f51e22
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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