Hydrochloric Acid → HCID 9913272, compound

HRID 2121192Notes

Reaction equation

HRID 2121192 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:28][CH2:29][S:30][CH3:31])[NH:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[ClH:33]>C(OCC)(=O)C>[ClH:33].[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:28][CH2:29][S:30][CH3:31])[NH:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9913273[4-(Pyrid-3-ylaminomethyl)-2-phenylbenzoyl]methionine methyl ester

Product 1

HCID 9913272HCID 9913272, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution in ethyl acetate (20 mL) of [4-(pyrid-3-ylaminomethyl)-2-phenylbenzoyl]methionine methyl ester (2.96 g, 6.58 mmol), prepared as in Example 226A, was added HCl (1.0 M in ethyl acetate, 20 mL, 20 mmol) dropwise. The reaction mixture was stirred for 10 minutes and then was concentrated and the residue was azeotroped with toluene. Water (50 mL) was added and the milky mixture was concentrated and lyophilized to give [4-(pyrid-3-ylaminomethyl)-2-phenylbenzoyl]methionine methyl ester hydrochloride (3.04 g, 95%). 1H NMR (300 MHz, DMSO d6) δ 8.66 (d, 1H), 8.11 (s, 1H), 8.02 (t, 1H), 7.84 (bt, 1H), 7.71 (m, 2H), 7.44 (m, 3H), 7.26 (m, 5H), 4.53 (bd, 2H), 4.36 (ddd, 1H), 3.64 (s, 3H), 2.23 (m, 2H), 1.98 (s, 3H), 3.85 (m, 2H). MS (CI NH3) m/e 450 (M+H)+, 374, 319, 287. Anal calcd for C25H28ClN3O3S+0.58 H2O): C, 60.48; H, 5.92; N, 8.46; Cl, 7.29. Found: C, 60.49; H, 5.58; N, 8.40; Cl 7.84.

Workup

  1. concentrationwas concentrated
  2. customthe residue was azeotroped with toluene
  3. additionWater (50 mL) was added
  4. concentrationthe milky mixture was concentrated

Sources & evidence

ORD record
ord-b1fad977952e40678423302e3ae1d420
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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