Lithium hydroxide, monohydrate → HCID 117761537, compound

HRID 1474626Notes

Reaction equation

HRID 1474626 reaction equation
C([O:4][C@H:5]1[C@H:11]([O:12]C(=O)C)[C@@H:10]([O:16]C(=O)C)[C@:9]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37](=[N:39][O:40][CH3:41])[CH3:38])=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:42][O:43]C(=O)C)[CH2:7][O:8]2)(=O)C.O.[OH-].[Li+]>C1COCC1.CO.O>[CH3:41][O:40][N:39]=[C:37]([CH3:38])[CH2:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][C:23]2[CH:22]=[C:21]([C@@:9]34[O:20][C@@:6]([CH2:42][OH:43])([CH2:7][O:8]3)[C@@H:5]([OH:4])[C@H:11]([OH:12])[C@H:10]4[OH:16])[CH:26]=[CH:25][C:24]=2[Cl:27])=[CH:34][CH:33]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 117762239HCID 117762239, compound

Product 1

HCID 117761537HCID 117761537, compoundYield 67.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-(2-(methoxy imino)propoxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (120 mg, 0.18 mmol) in THF (0.8 mL), methanol (1.2 mL) and water (0.4 mL) was added lithium hydroxide monohydrate (15.2 mg, 0.36 mmol) at 0° C. The reaction mixture was stirred at r.t. for 1 h. Volatiles were evaporated in vacuo and the residue obtained was purified by column chromatography (silica gel, 1:9 MeOH:DCM) to provide the title compound (60 mg, 67%).

Workup

  1. customVolatiles were evaporated in vacuo
  2. customthe residue obtained
  3. customwas purified by column chromatography (silica gel, 1:9 MeOH:DCM)

Sources & evidence

ORD record
ord-dacf50c1a5f741ffa4a347521da73d53
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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