Lithium Hydroxide → HCID 69546178, compound

HRID 1823204Notes

Reaction equation

HRID 1823204 reaction equation
C([O:3][C:4]([C@H:6]1[N:10]2[C:11](=[O:28])[C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)=[N:13][C:14]([Cl:15])=[C:9]2[C@@:8]([NH:30][C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])([CH3:29])[CH2:7]1)=[O:5])C.[OH-].[Li+]>C1COCC1.CO.O.CCOC(C)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:34]([O:33][C:31]([NH:30][C@@:8]1([CH3:29])[C:9]2=[C:14]([Cl:15])[N:13]=[C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=3)[C:11](=[O:28])[N:10]2[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

8

Reactant 2

HCID 3939Lithium HydroxideHCID 69654517HCID 69654517, compound

Product 1

HCID 69546178HCID 69546178, compoundYield 99%

Reagents, catalysts & solvents 5

HCID 887MethanolCatalystHCID 311Citric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a flask (6S,8R)-8-benzyloxycarbonylamino-1-chloro-8-methyl-4-oxo-3-(3-trifluoromethyl-benzyloxy)-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrazine-6-carboxylic acid ethyl ester (50 mg, 0.0862 mmol) was dissolved in THF (800 μL) and 2 drops MeOH and cooled to 0° C. Lithium hydroxide (260 μL, 0.259 mmol) 1.0 M in water was added and the mixture allowed to stir for approximately 2 h at 0° C. TLC indicated complete reaction. The mixture was diluted with EtOAc and 5% citric acid was added. The mixture was separated and the aqueous layer extracted 1× with EtOAc. The organics were dried with Na2SO4 filtered and concentrated to give the product as a white solid (47 mg, 99% yield). 1HNMR (300 MHz, CD3OD) δ 1.6(s, 3H) 2.25 (m, 1H) 2.95(m, 1H) 4.63 (s, 2H) 5.05 (m, 2H) 7.25–7.8 (m, 9H)

Workup

  1. customreaction
  2. additionwas added
  3. customThe mixture was separated
  4. extractionthe aqueous layer extracted 1× with EtOAc
  5. dry with materialThe organics were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-767c1123ad2445e6af0ae0dbf5b813c5
Source dataset
uspto-grants-2006_05
Patent number
US07037911B2

Reaction notes

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