Water → HCID 117776457, compound

HRID 1474637Notes

Reaction equation

HRID 1474637 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:44][O:45][CH3:46])[C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:47][O:48]C(=O)C)[CH2:7][O:8]2)(=O)C.C1COCC1.O.O[Li].O>CO.C(OC(=O)C)C>[CH3:46][O:45][N:44]=[C:37]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[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]([CH2:47][OH:48])([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

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 131732775HCID 131732775, compound

Product 1

HCID 117776457HCID 117776457, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-(2-(methoxyimino)-2-phenylethoxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (170 mg, 0.23 mmol) in MeOH:THF:H2O (0.7 mL, 0.5 mL, 0.17 mL), LiOH.H2O (14.7 mg, 0.35 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, solvent was evaporated in vacuo. The residue obtained was diluted with ethylacetate (100 mL), washed with water (10 mL) and brine (10 mL). The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, MeOH:DCM) to afford the title compound (80 mg, 0.14 mmol, 61.8%).

Workup

  1. customAfter completion of the reaction
  2. customwas evaporated in vacuo
  3. customThe residue obtained
  4. washwashed with water (10 mL) and brine (10 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe volatiles were evaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by column chromatography (silica gel, MeOH:DCM)

Sources & evidence

ORD record
ord-1c7b5eaf9e2c4fe8b144e699d5505c2e
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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