Hydrochloric Acid → HCID 57920057, compound

HRID 19378Notes

Reaction equation

HRID 19378 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:38])[C@@H:15]([N:20]3[CH2:24][C:23]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][C:33]([OH:36])([CH3:35])[CH3:34])[CH:27]=4)=[CH:22][C:21]3=[O:37])[CH2:16][CH:17]([CH3:19])[CH3:18])=[N:9]2)[CH2:4][O:3]1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:6][C@@H:5]([CH2:4][OH:3])[CH2:7][N:8]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:38])[C@@H:15]([N:20]2[CH2:24][C:23]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][C:33]([OH:36])([CH3:34])[CH3:35])[CH:27]=3)=[CH:22][C:21]2=[O:37])[CH2:16][CH:17]([CH3:18])[CH3:19])=[N:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57920097HCID 57920097, compound

Product 1

HCID 57920057HCID 57920057, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-2-{4-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-amide (prepared as in Example 237, 0.175 g, 0.32 mmol) in tetrahydrofuran (5 mL) was treated with hydrochloric acid (1 M, 1 mL). The reaction mixture was stirred at room temperature overnight and then neutralized with saturated sodium bicarbonate. The mixture was extracted with ethyl acetate (2×50 mL). The combined ethyl acetate extracts were dried over sodium sulfate, filtered and concentrated in vacuo which afforded (S)-2-{4-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-amide (0.097 g, 61%) as a white solid: HR-ES-MS m/z calculated for C26H36N4O6 [M+H]+ 501.2708, observed 501.2705; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.90 (d, J=6.4 Hz, 3H), 0.94 (d, J=6.4 Hz, 3H), 1.06 (s, 6H), 1.36-1.65 (m, 2H), 1.65-1.83 (m, 1H), 2.68 (s, 2H), 3.19-3.33 (m, 2H), 3.78 (d, J=5.1 Hz, 1H), 3.86 (dd, J=13.5, 7.5 Hz, 1H), 4.09 (dd, J=13.5, 3.8 Hz, 1H), 4.18 (d, J=18.4 Hz, 1H), 4.37 (s, 1H), 4.56 (d, J=18.4 Hz, 1H), 4.71 (t, J=5.4 Hz, 1H), 4.83 (s, 1H), 4.87 (dd, J=11.0, 4.7 Hz, 1H), 4.94 (d, J=5.1 Hz, 1H), 6.40 (d, J=2.1 Hz, 1H), 7.06-7.19 (m, 3H), 7.28-7.43 (m, 1H), 7.53 (d, J=2.1 Hz, 1H), 10.75 (s, 1H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  2. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo which

Sources & evidence

ORD record
ord-4bb2bbfd64ce43b38bf78eeffb25c4e0
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

Loading…