Water → HCID 117762815, compound

HRID 1474633Notes

Reaction equation

HRID 1474633 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][C:36]5[C:40](=[N:41][O:42][CH3:43])[CH2:39][CH2:38][CH:37]=5)=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:44][O:45]C(=O)C)[CH2:7][O:8]2)(=O)C.C1COCC1.O.O[Li].O>CO>[CH3:43][O:42][N:41]=[C:40]1[CH2:39][CH2:38][CH:37]=[C:36]1[O:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][C:23]2[CH:22]=[C:21]([C@@:9]34[O:20][C@@:6]([CH2:44][OH:45])([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:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 131732774HCID 131732774, compound

Product 1

HCID 117762815HCID 117762815, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-((5-(methoxyimino)cyclopent-1-en-1-yl)oxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (110 mg, 0.16 mmol) in MeOH:THF:H2O (0.48 mL, 0.36 mL, 0.12 mL), LiOH.H2O (10.3 mg, 0.24 mmol) was added at 0° C. The reaction mixture was stirred for 1 h at r.t. After completion of the reaction as confirmed by TLC, the solvent was evaporated in vacuo. The crude compound obtained was purified by column chromatography (silica gel, 0.4:9.6 MeOH:DCM) to provide title compound (75 mg, 90.5%) as off-white solid.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated in vacuo
  3. customThe crude compound obtained
  4. customwas purified by column chromatography (silica gel, 0.4:9.6 MeOH:DCM)

Sources & evidence

ORD record
ord-7c9bf96410d14d5c991d03cbb846c150
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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