Hydrochloric Acid → HCID 59520077, compound

HRID 1669908Notes

Reaction equation

HRID 1669908 reaction equation
C[O:2][C:3]([C@:5]1([CH3:25])[C@H:9]([OH:10])[CH2:8][CH2:7][N:6]1[S:11](=[O:24])(=[O:23])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([Cl:21])[C:14]=1[CH3:22])=[O:4].Cl>[OH-].[Na+]>[Cl:21][C:15]1[C:14]([CH3:22])=[C:13]([NH:12][S:11]([N:6]2[CH2:7][CH2:8][C@@H:9]([OH:10])[C@@:5]2([CH3:25])[C:3]([OH:4])=[O:2])(=[O:23])=[O:24])[CH:18]=[CH:17][C:16]=1[C:19]#[N:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59520073HCID 59520073, compound

Product 1

HCID 59520077HCID 59520077, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3C (120 mg, 0.309 mmol) in 8 mL of 1.6 N NaOH was stirred at rt overnight. The reaction mixture was acidified to pH 2 with 10% HCl and extracted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure to afford the title compound (76 mg) as an orange oil. 1H NMR (CD3OD) δ 1.58 (s, 3H), 1.98-2.04 (m, 1H), 2.13-2.19 (m, 1H), 2.43 (s, 3H), 3.49-3.54 (m, 1H), 3.65-3.70 (m, 1H), 4.12 (t, J=6.1, 1H), 7.59 (d, J=8.3, 1H), 7.65 (d, J=8.8, 1H); 13C NMR (CD3OD) δ 15.33, 23.61, 31.78, 48.13, 74.81, 81.10, 109.72, 117.40, 122.04, 130.98, 132.84, 137.85, 143.90, 175.19; HPLC a) column: Phenominex ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA; 1 min hold, 4 mL/min UV detection at 220 nm, 2.55 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold; 4 mL/min, UV detection at 220 nm, 2.40 min retention time (89%); MS (ES) m/z 374 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbfff8895e20458892668da81b7c2789
Source dataset
uspto-grants-2011_08
Patent number
US07989640B2

Reaction notes

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