Hydrochloric Acid → HCID 57920018, compound

HRID 19198Notes

Reaction equation

HRID 19198 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:37])[CH:15]([N:23]3[CH2:27][C:26]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[Cl:35])=[CH:25][C:24]3=[O:36])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:9]2)[CH2:4][O:3]1.Cl.ClC1C=CC=CC=1OC1CN(C(CC2C=CC=CC=2)C(NC2C=CN(C[C@@H](O)CO)N=2)=O)C(=O)C=1>O1CCCC1.C(OCC)(=O)C>[Cl:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[O:28][C:26]1[CH2:27][N:23]([C@@H:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([NH:13][C:10]2[CH:11]=[CH:12][N:8]([CH2:7][C@@H:5]([OH:6])[CH2:4][OH:3])[N:9]=2)=[O:37])[C:24](=[O:36])[CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66899107HCID 66899107, compoundHCID 66899670HCID 66899670, compound

Product 1

HCID 57920018HCID 57920018, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-phenyl-propionic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-amide (0.010 g, 0.017 mmol) in tetrahydrofuran (1 mL) was treated with 2N aqueous hydrochloric acid solution (1 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, 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-phenyl-N-[1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-propionamide (0.007 g, 82%) as an off-white powder: HR-ES-MS m/z calculated for C23H27ClN4O6 [M+H]+ 497.1587, observed 497.1586; 1H NMR (300 MHz, CDCl3) δ ppm 1.75 (br. s., 2H), 3.17 (dd, J=14.0, 8.8 Hz, 1H), 3.39 (dd, J=14.0, 6.9 Hz, 1H), 3.44-3.55 (m, 2H), 3.56-3.65 (m, 1H), 3.95-4.10 (m, 2H), 4.16 (d, J=18.1 Hz, 1H), 4.30 (d, J=18.1 Hz, 1H), 4.77 (s, 1H), 5.02 (t, J=7.8 Hz, 1H), 6.65 (d, J=1.8 Hz, 1H), 7.17 (dd, J=8.2, 1.8 Hz, 1H), 7.19-7.26 (m, 6H), 7.28-7.35 (m, 2H), 7.46 (dd, J=7.8, 1.5 Hz, 1H), 9.65 (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-7aaa07ef50a442aaac6d523ef5a3a802
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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