Hydrochloric Acid → HCID 68433380, compound

HRID 1162817Notes

Reaction equation

HRID 1162817 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:9][CH:8]2[CH2:24][C:25]([O:27]CC)=[O:26])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:9][CH:8]2[CH2:24][C:25]([OH:27])=[O:26])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86617473HCID 86617473, compound

Product 1

HCID 68433380HCID 68433380, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [1-(4-fluorobenzyl)-4-(benzyloxycarbonyl)-6-oxo-piperazin-2-yl]acetate (0.5 g, 1.2 mmol) in tetrahydrofuran (2.3 mL) was added 1N sodium hydroxide (2.3 mL, 2.3 mmol). After 2 h, 1N hydrochloric acid (3 mL) was added. The reaction mixture was partitioned between dichloromethane and brine. The organic phase was dried over sodium sulfate, filtered and concentrated to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.23-7.38 (m, 7H), 7.01 (t, J=8.6 Hz, 2H), 5.12-5.20 (m, 3H), 4.45-4.53 (m, 1H), 4.22-4.32 (m, 1H), 3.97 (d, J=15.0 Hz, 2H), 3.78-3.83 (m, 1H), 3.04-3.18 (m, 1H), 2.52-2.67 (m, 2H). ES MS (M+1)=401.2.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb4898a608d54c7eb03c4d744d505688
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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