Sodium Acetate → (4-Carboxymethylamino-2-phenylbenzoyl)methionine methyl ester

HRID 325236Notes

Reaction equation

HRID 325236 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.[C:27]([OH:31])(=[O:30])[CH:28]=O.C([BH3-])#N.[Na+].C([O-])(=O)C.[Na+]>CO.C(OCC)(=O)C.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:28][C:27]([OH:31])=[O:30])=[CH:9][C:8]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 15620607Glyoxylic acid, monohydrateHCID 18666758N-(4-Amino-2-phenylbenzoyl)methionine methyl ester2×

Product 1

HCID 70228430(4-Carboxymethylamino-2-phenylbenzoyl)methionine methyl esterYield 83.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (4-amino-2-phenylbenzoyl)methionine methyl ester (compound 8, 1.51 g, 4.21 mmol), glyoxylic acid monohydrate (466 mg, 5.06 mmol), sodium cyanoborohydride (1.0 M in THF, 4.2 mL), sodium acetate (0.5 g) and acetic acid (0.5 mL) in methanol (10 mL) was stirred for 14 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with saturated aqueous potassium dihydrogenphosphate, water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate, then 3% methanol-ethyl acetate) to give (4-carboxymethylamino-2-phenylbenzoyl)methionine methyl ester (1.46 g, 83%). 1H NMR (300 MHz, CDCl3) δ 7.67 (d, 1H), 7.39 (m, 5H), 6.54 (dd, 1H), 6.45 9d, 1H), 5.96 (br d, 1H), 4.63 (m, 1H), 3.88 (d, 2H), 3.67 (s, 3H), 2.04 (m, 2H), 2.00 (s, 3H), 1.86 (m, 1H), 1.67 (m, 1H). MS (APCI+) m/e 417 (M+H)+.

Workup

  1. washwashed with saturated aqueous potassium dihydrogenphosphate, water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-bb8a54ef02d74b2993efccafcd3434d8
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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