Methanol → HCID 117762168, compound

HRID 1474643Notes

Reaction equation

HRID 1474643 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[CH:41]=[CH:40][C:39]([C:42](=[N:44][O:45][CH2:46][CH3:47])[CH3:43])=[CH:38][CH:37]=5)=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:48][O:49]C(=O)C)[CH2:7][O:8]2)(=O)C.CO.O.O.[OH-].[Li+]>C1COCC1>[CH2:46]([O:45][N:44]=[C:42]([C:39]1[CH:38]=[CH:37][C:36]([O:35][C:32]2[CH:31]=[CH:30][C:29]([CH2:28][C:23]3[CH:22]=[C:21]([C@@:9]45[O:20][C@@:6]([CH2:48][OH:49])([CH2:7][O:8]4)[C@@H:5]([OH:4])[C@H:11]([OH:12])[C@H:10]5[OH:16])[CH:26]=[CH:25][C:24]=3[Cl:27])=[CH:34][CH:33]=2)=[CH:41][CH:40]=1)[CH3:43])[CH3:47]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 117761600HCID 117761600, compound

Product 1

HCID 117762168HCID 117762168, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-(4-(1-(ethoxyimino)ethyl)phenoxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (210.0 mg, 0.28 mmol), in THF (1.6 mL), methanol (2.4 mL) and water (0.8 mL) was added lithium hydroxide monohydrate (14.0 mg, 0.34 mmol) at 0° C. The reaction mixture was stirred at r.t. for 1 h. After the completion of reaction as confirmed by TLC, volatiles were evaporated in vacuo and the compound was diluted with ethyl acetate (50 mL). The organic layer was washed with water (2×10 mL), dried over Na2SO4 and concentrated to afford title compound (160.0 mg, 98%) as a white solid.

Workup

  1. customAfter the completion of reaction
  2. customwere evaporated in vacuo
  3. additionthe compound was diluted with ethyl acetate (50 mL)
  4. washThe organic layer was washed with water (2×10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cef0d6c630aa4c5d8b09a244a073ef64
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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