Hydrochloric Acid → HCID 59838035, compound

HRID 735539Notes

Reaction equation

HRID 735539 reaction equation
[OH-].[Na+].[CH2:3]([N:10]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:11]1[CH:12]=[C:13](/[CH:18]=[CH:19]/[C:20]([O:22]C)=[O:21])[CH:14]=[C:15]([F:17])[CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>O1CCCC1.CO>[CH2:24]([N:10]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:11]1[CH:12]=[C:13](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])[CH:14]=[C:15]([F:17])[CH:16]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59838032HCID 59838032, compound

Product 1

HCID 59838035HCID 59838035, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydroxide (2 mL, 2 mmol, 1.00 N solution) was added to a solution of 19B (0.467 g, 1.24 mmol) in tetrahydrofuran (2 mL) and methanol (1 mL). The reaction was heated at 80° C. for 1 h. Hydrochloric acid (1 N) was added and the reaction mixture was extracted with ethyl acetate (2×). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to give 19C (0.411 g, 91%) as a pale yellow solid. LC-MS m/z: 362.4 (M+H)+.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (2×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-874dbe23ce05408c93788a82f35e4b05
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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