Sodium Chloride → HCID 59620371, compound

HRID 2070168Notes

Reaction equation

HRID 2070168 reaction equation
O.[C:2]([O:6][C:7]([NH:9][C@@H:10]([C:15]([OH:17])=O)[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])([CH3:5])([CH3:4])[CH3:3].C(Cl)(=O)OCC(C)C.C([C@H]([C@@H](C(O)=O)O)O)(O)=O.[NH2:36][CH:37]1[CH2:46][C:45]2[C:40](=[C:41]([N:47]3[CH2:51][CH2:50][CH2:49][C:48]3=[O:52])[CH:42]=[CH:43][CH:44]=2)[N:39]([CH2:53][C:54]2[CH:58]=[CH:57][S:56][CH:55]=2)[C:38]1=[O:59].[OH-].[Na+].[Cl-].[Na+]>O1CCCC1.O.C(N(CC)CC)C>[CH3:14][CH:12]([CH3:13])[CH2:11][C@@H:10]([NH:9][C:7](=[O:8])[O:6][C:2]([CH3:3])([CH3:4])[CH3:5])[C:15](=[O:17])[NH:36][CH:37]1[CH2:46][C:45]2[C:40](=[C:41]([N:47]3[CH2:51][CH2:50][CH2:49][C:48]3=[O:52])[CH:42]=[CH:43][CH:44]=2)[N:39]([CH2:53][C:54]2[CH:58]=[CH:57][S:56][CH:55]=2)[C:38]1=[O:59]

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 14798Sodium Hydroxide2×HCID 62365Isobutyl chloroformateHCID 2724763BOC-D-LEU-OH H2OHCID 86649074HCID 86649074, compound

Product 1

HCID 59620371HCID 59620371, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
5 °C

Procedure

N-tert-Butoxycarbonyl-D-leucine monohydrate (25.00 g) was dissolved in tetrahydrofuran (224 mL), and triethylamine (20.30 g) and isobutyl chlorocarbonate (13.06 g) were sequentially added thereto at 5° C. or lower under cooling on ice. To the mixture was added 3-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one D-(−)-tartrate (44.80 g) in an aqueous sodium hydroxide solution (a mixture of 25% aqueous sodium hydroxide solution (14.58 g) and water (89.6 g)) at 5° C. or lower. The mixture was stirred for 10 minutes under cooling on ice, and then the temperature was raised to room temperature. Saturated aqueous sodium chloride solution (44.8 g) was added to the reaction mixture to partition the mixture, and the aqueous layer was further extracted with tetrahydrofuran (224 mL). The organic layers were combined, and the combined organic layer was concentrated to half volume, whereby a solution of the title compound in tetrahydrofuran was yielded.

Workup

  1. temperatureunder cooling on ice
  2. temperaturethe temperature was raised to room temperature
  3. customto partition the mixture
  4. extractionthe aqueous layer was further extracted with tetrahydrofuran (224 mL)
  5. concentrationthe combined organic layer was concentrated to half volume, whereby a solution of the title compound in tetrahydrofuran
  6. customwas yielded

Sources & evidence

ORD record
ord-95eddc5e5f0940c590b7d4592220e485
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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