Lithium Hydroxide → HCID 68441607, compound

HRID 2246912Notes

Reaction equation

HRID 2246912 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:9]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=3[CH:36]=2)[CH2:8][NH:7]1)=[O:5])C.[OH-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47]>CO.O1CCCC1.O.C(OCC)(=O)C>[CH2:49]([O:48][C:46]([N:7]1[CH2:8][C@H:9]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=3[CH:36]=2)[C@@H:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:11][C@H:6]1[C:4]([OH:3])=[O:5])=[O:47])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 11951635HCID 11951635, compound

Product 1

HCID 68441607HCID 68441607, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 1.5 g of (2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-2-carboxylic acid ethyl ester (from example 2) in 60 ml of methanol-tetrahydrofuran-water 1:1:1 are added 2.85 ml of a solution of 1N lithiumhydroxide at 0° C. Stirring is continued for an additional 2 hours at room temperature, followed by addition of 40 ml of ethyl acetate, 20 ml of saturated aqueous sodium carbonate solution and 0.42 ml of benzyl chloroformate. The reaction mixture is stirred for 1 hour, diluted with ethyl acetate and the organic phase is dried over sodium sulfate. The organic phase is concentrated under reduced pressure and the residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a yellow oil. Rf=0.13 (EtOAc); Rt=4.77.

Workup

  1. stirringThe reaction mixture is stirred for 1 hour
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. concentrationThe organic phase is concentrated under reduced pressure
  4. customthe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-d1ce92f934b947eb811ad98f2aeba73e
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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