Hydrochloric Acid → HCID 9916259, compound

HRID 1251886Notes

Reaction equation

HRID 1251886 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)=[C:20]([CH:33]=2)[C:21]([NH:23][C@@H:24]([CH2:29][CH2:30][S:31][CH3:32])[C:25]([O:27]C)=[O:26])=[O:22])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:34][CH2:35][C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)=[C:20]([CH:33]=2)[C:21]([NH:23][C@@H:24]([CH2:29][CH2:30][S:31][CH3:32])[C:25]([OH:27])=[O:26])=[O:22])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57176847HCID 57176847, compound

Product 1

HCID 9916259HCID 9916259, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl (2S)-2-{5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfanylbutyrate (140 mg, 0.24 mmol) in methanol (5 ml) was treated with sodium hydroxide (190 mg, 4.7 mmol) in water (1 ml) and the mixture stirred at ambient temperature for 6 hours. The mixture was acidified to PH1 with 1M HCl and evaporated to dryness. The residue was washed with water (3×2 mL) and the resulting gum was triturated with diethyl ether to give the title compound as a white solid (43 mg). 1H NMR (DMSO-d6, 300 MHz) δ: 1.85-2.05 (5H,m); 2.4-2.6 (signed partially obscured by solvent signals, m); 2.6-2.75 (2H,m); 2.75-2.86 (2H,m); 4.4-4.48 (1H, m); 4.64.7 (2H,m); 5.82 (1H,t); 6.76-6.86 (2H,m); 6.96-7.08 (3H,m); 7.12-7.28 (4H,m); 7.44-7.5 (2H,dd); 7.62 (1H,s); 7.69 (1H,s); 8.58 (1H,t); 9.12 (1H,s). MS (ES+) m/z 580.3 (MH+) Anal.calculated for C31H31F2N3O4S.HCl.0.9NaCl C, 55.7; H, 4.8; N, 6.3%; Found: C, 55.9; H, 4.8; N, 6.1%.

Workup

  1. customevaporated to dryness
  2. washThe residue was washed with water (3×2 mL)
  3. customthe resulting gum was triturated with diethyl ether

Sources & evidence

ORD record
ord-fe6b8405125542779be503dc1a1e2754
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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