Hydrochloric Acid → HCID 59607747, compound

HRID 1945014Notes

Reaction equation

HRID 1945014 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@@H:15]([NH:22][C:23]([C:25]3[S:29][C:28]([O:30]C)=[N:27][CH:26]=3)=[O:24])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C@@H:15]([NH:22][C:23]([C:25]3[S:29][C:28](=[O:30])[NH:27][CH:26]=3)=[O:24])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59607574HCID 59607574, compound

Product 1

HCID 59607747HCID 59607747, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (R)-ethyl 4-(3′-chlorobiphenyl-4-yl)-3-(2-methoxythiazole-5-carboxamido)butanoate, intermediate 13, (170 mg, 0.37 mmol) in dioxane (5 mL) is added a solution of 4 M HCl in dioxane (0.5 mL, 2.00 mmol). The crude is stirred at room temperature for 3 hrs. The crude is concentrated. Part of the crude is purified via RP-HPLC (SunFire C18, H2O (0.1% TFA)/CH3CN) to give (95 mg) of (R)-ethyl 4-(3′-chlorobiphenyl-4-yl)-3-(2-oxo-2,3-dihydrothiazole-5-carboxamido)butanoate as a white solid. HPLC retention time=1.82 minutes (condition D); MS (m+1)=445.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.29 (t, J=7.1 Hz, 3H) 2.46-2.70 (m, 2H) 2.78-2.97 (m, 1H) 3.07 (dd, J=13.0, 6.2 Hz, 1H) 4.11-4.28 (m, 2H) 4.51-4.69 (m, 1H) 6.64 (d, J=8.1 Hz, 1H), 7.19-7.42 (m, 5H) 7.44 (d, J=6.1 Hz, 1H) 7.48-7.62 (m, 3H), 9.54 (br. s., 1H).

Workup

  1. concentrationThe crude is concentrated
  2. customPart of the crude is purified via RP-HPLC (SunFire C18, H2O (0.1% TFA)/CH3CN)

Sources & evidence

ORD record
ord-d7dfdb21ecbe4967b39a815d19c1211c
Source dataset
uspto-grants-2013_03
Patent number
US08394853B2

Reaction notes

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