Acetic Anhydride → HCID 178476300, compound

HRID 1404404Notes

Reaction equation

HRID 1404404 reaction equation
[OH:1][CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][CH:12]=[O:13])[CH2:6][CH2:5]1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:22]([O:1][CH2:2][CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([CH:10]([NH:14][C:15]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:21])[CH2:11][CH:12]=[O:13])[CH2:8][CH2:9]1)(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178453538HCID 178453538, compound

Product 1

HCID 178476300HCID 178476300, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 1-(trans-4-(2-hydroxyethyl)cyclohexyl)-3-oxopropylcarbamate (1.88 g, 6.28 mmol) in DCM (60 mL) was added DMAP (cat. amount), followed by addition of TEA (2.63 mL, 18.84 mmol) and acetic anhydride (0.89 mL, 9.42 mmol) at 0° C. under N2. The mixture was stirred at rt for 3 h, and diluted with DCM, quenched by addition of aqueous NaHCO3 solution. The organic phase was separated and dried over Na2SO4. Purification by flash column chromatography (eluent: 40% EtOAc in hexanes) gave the product as colorless gel (1.90 g, 88.6%).

Workup

  1. customquenched by addition of aqueous NaHCO3 solution
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. customPurification by flash column chromatography (eluent: 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-45474fe1ae1c45aa9b9f2eb5397f6c64
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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