Hydrochloric Acid → HCID 59520084, compound

HRID 1669910Notes

Reaction equation

HRID 1669910 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([OH:10])[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][C@@H:8]([OH:10])[CH2:9][C@H:5]2[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 59520082HCID 59520082, compound

Product 1

HCID 59520084HCID 59520084, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4A (60 mg, 0.160 mmol) in 4 mL of 1.6 N NaOH was stirred at rt for 1 h. The reaction mixture was acidified to pH 2 with 10% HCl. A solid precipitated which was filtered, washed with water and dried to afford the title compound (58 mg) as an orange solid. 1H NMR (CD3OD) δ 2.38-2.42 (m, 5H) 3.31-3.34 (m, 1H), 3.62-3.65 (m, 1H), 4.40-4.42 (m, 1H), 4.49-4.52 (m, 1H), 7.60 (d, 8.8, 1H), 7.71 (d, J=8.8, 1H); 13C NMR (CD3OD) δ 15.28, 39.89, 57.29, 61.95, 71.03, 109.61, 117.42, 121.42, 130.55, 132.93, 137.84, 143.77, 175.99; 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, 2.40 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, 2.23 min retention time (63%); MS (ES) m/z 360 [M+H]+.

Workup

  1. customA solid precipitated which
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-82c60f7eb8814256a73a12c5cb8cea39
Source dataset
uspto-grants-2011_08
Patent number
US07989640B2

Reaction notes

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