Lithium Hydroxide → HCID 52913286, compound

HRID 1695850Notes

Reaction equation

HRID 1695850 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][NH:9][C:8]2[CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[C:20]([C@H:22]4[C@H:27]([OH:28])[C@@H:26]([OH:29])[C@H:25]([OH:30])[C@@H:24]([CH2:31][OH:32])[O:23]4)[CH:19]=[CH:18][C:17]=3[Cl:33])[CH:13]=[CH:14][C:7]=2[O:6]1)=[O:4].[OH-].[Li+]>C1COCC1.CO.O>[Cl:33][C:17]1[CH:18]=[CH:19][C:20]([C@H:22]2[C@H:27]([OH:28])[C@@H:26]([OH:29])[C@H:25]([OH:30])[C@@H:24]([CH2:31][OH:32])[O:23]2)=[CH:21][C:16]=1[CH2:15][C:12]1[CH:13]=[CH:14][C:7]2[O:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:10][NH:9][C:8]=2[CH:11]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 529131716-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid methyl ester

Product 1

HCID 52913286HCID 52913286, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of 6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid methyl ester (190 mg) in THF: Methanol:water (1:1:1 mixture, 1.5 mL) was added lithium hydroxide (17 mg). After stirring at room temperature overnight, the reaction mixture was concentrated, and the resulting residue was taken up in 50% methanol in ethyl acetate. The solution was filtered through a celite bed, and the filtrate was concentrated to a residue which was purified by preparative HPLC to furnish 6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid (23 mg).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. filtrationThe solution was filtered through a celite bed
  3. concentrationthe filtrate was concentrated to a residue which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-11bbf3678018414c8d37dd4ed9b1d21e
Source dataset
uspto-grants-2012_04
Patent number
US08163704B2

Reaction notes

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