Hydrochloric Acid → HCID 57920038, compound

HRID 19199Notes

Reaction equation

HRID 19199 reaction equation
[Cl:1][C:2]1[CH:39]=[CH:38][CH:37]=[CH:36][C:3]=1[O:4][C:5]1[CH2:9][N:8]([C@@H:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:11]([NH:13][C:14]2[CH:18]=[CH:17][N:16]([CH2:19][C@@H:20]3[CH2:24][O:23]C(C)(C)[O:21]3)[N:15]=2)=[O:12])[C:7](=[O:35])[CH:6]=1.Cl.ClC1C=CC=CC=1OC1CN([C@@H](CC2C=CC(Cl)=CC=2)C(NC2C=CN(C[C@@H](O)CO)N=2)=O)C(=O)C=1>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:39]=[CH:38][CH:37]=[CH:36][C:3]=1[O:4][C:5]1[CH2:9][N:8]([C@@H:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:11]([NH:13][C:14]2[CH:18]=[CH:17][N:16]([CH2:19][C@@H:20]([OH:21])[CH2:24][OH:23])[N:15]=2)=[O:12])[C:7](=[O:35])[CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 57920149(S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-N-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-3-(2-chlorophenyl)-propionamideHCID 66899237HCID 66899237, compound

Product 1

HCID 57920038HCID 57920038, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(4-chlorophenyl)-propionic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-amide (prepared as in Example 188, 0.151 g, 0.259 mmol) in tetrahydrofuran (3 mL) was treated with 2N aqueous hydrochloric acid solution (3 mL). The reaction mixture was stirred at 25° C. for 3 h. The reaction mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution, a saturated sodium chloride solution and dried over magnesium sulfate. The organic layer was concentrated to afford, (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(4-chlorophenyl)-N-[1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-propionamide (0.110 g, 80%) as a white powder: HR-ES-MS m/z calculated for C25H24Cl2N4O5 [M+H]+ 531.1196, observed 531.1197; 1H NMR (300 MHz, DMSO-d6); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.19-3.30 (m, 4H), 3.74 (br. s., 1H), 3.80-3.91 (m, 1H), 4.07 (dd, J=13.6, 3.6 Hz, 1H), 4.25 (d, J=18.2 Hz, 1H), 4.39 (d, J=18.2 Hz, 1H), 4.65-4.71 (m, 1H), 4.72 (s, 1H), 4.93 (d, J=5.1 Hz, 1H), 5.18 (t, J=7.5 Hz, 1H), 6.43 (d, J=1.5 Hz, 1H), 7.18-7.30 (m, 2H), 7.30-7.47 (m, 5H), 7.53 (d, J=1.5 Hz, 1H), 7.62 (d, J=7.8 Hz, 1H), 10.76 (s, 1H).

Workup

  1. washwashed with water, saturated sodium bicarbonate solution
  2. dry with materiala saturated sodium chloride solution and dried over magnesium sulfate
  3. concentrationThe organic layer was concentrated
  4. customto afford

Sources & evidence

ORD record
ord-d01749b3a6cb4d3bace1ecbd614d346d
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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