Acetic Anhydride → HCID 178476300, compound

HRID 1486216Notes

Reaction equation

HRID 1486216 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-c87a43d01fb949759c57b933f2bf4f1c
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

Loading…