Acetic Anhydride → (S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate

HRID 705321Notes

Reaction equation

HRID 705321 reaction equation
[Cl:1][CH2:2][C@@H:3]([OH:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]3[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]3)=[CH:17][CH:16]=2)([CH3:14])[CH3:13])=[CH:8][CH:7]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:31]([O:30][C@@H:3]([CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]3[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]3)=[CH:17][CH:16]=2)([CH3:14])[CH3:13])=[CH:10][CH:11]=1)[CH2:2][Cl:1])(=[O:33])[CH3:32]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 117689849(S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol

Product 1

HCID 117689799(S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of (S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol (850 mg, 1.95 mmol) in anhydrous pyridine (6.0 mL) were successively added acetic anhydride (280 μL, 2.93 mmol) and catalytic amount of DMAP. After 3 h, the reaction mixture was quenched with an aqueous solution of sodium chloride and stirred for 15 min, and the resulting mixture was extracted twice with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate and filtered. Solvents were evaporated, and the resulting crude material was used without further purification.

Workup

  1. customthe reaction mixture was quenched with an aqueous solution of sodium chloride
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customSolvents were evaporated
  6. customthe resulting crude material was used without further purification

Sources & evidence

ORD record
ord-44d2fcca92ec4c009ef978b1c7392203
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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