Hydrochloric Acid → HCID 20773590, compound

HRID 1815710Notes

Reaction equation

HRID 1815710 reaction equation
C[O:2][C:3](=[O:28])[C@@H:4]1[CH2:8][CH:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH2:6][N:5]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[OH-].[Na+].Cl>CO>[C:21]([N:5]1[CH2:6][CH:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH2:8][C@H:4]1[C:3]([OH:28])=[O:2])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20773591HCID 20773591, compound

Product 1

HCID 20773590HCID 20773590, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product (10.57 g, 26.0 mmol) of Step 63a of Example 63 {BOC—N—P2[(4R)-(7-chloroquinoline-4-oxo) proline methyl ester} dissolved in MeOH (800 mL) cooled to 0° C. was added an aqueous 1N NaOH solution (44.5 mL, 44.5 mmol). The mixture was warmed to rt after 6 h, stirred overnite, and the pH adjusted to pH 7 using 1.0 N aqueous HCl. The solution was concentrated until only the water layer remained, the pH adjusted to 4 using 6N aqueous HCl and the mixture was partitioned repeatedly with EtOAc (3×500 mL). The combined organic layers were dried (MgSO4) and concentrated to afford 10.16 g (100%) of the as a white solid. 1H NMR (DMSO-d6) δ 1.32, 1.34 (two s (rotamers) 9H), 2.31-2.40 (m, 1H), 2.58-2.69 (m, 1H), 3.65-3.81 (m, 2H), 4.33-4.40 (m, 1H), 5.34 (m, 1H), 7.10-7.11 (m, 1H), 7.57 (d, J=9 Hz, 1H), 7.98 (s, 1H), 8.09-8.14 (m, 1H), 8.75 (d, J=5 Hz, 1H), 12.88 (brs, 1H). 13C NMR (DMSO-d6) δ 27.82, 35.84, 51.52, 57.75, 76.03, 79.33, 102.95, 119.54, 123.86, 126.34, 127.24, 134.49, 149.32, 152.88, 153.25, 159.08, 173.74. LC-MS (retention time: 1.48, method D), MS m/e 393 (M++1)

Workup

  1. temperatureThe mixture was warmed to rt after 6 h
  2. concentrationThe solution was concentrated until only the water layer
  3. customthe mixture was partitioned repeatedly with EtOAc (3×500 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. customto afford 10.16 g (100%) of the as a white solid

Sources & evidence

ORD record
ord-6b323e80096a45dcaf184478fc655527
Source dataset
uspto-grants-2005_04
Patent number
US06878722B2

Reaction notes

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