Acetic Anhydride → HCID 89730082, compound

HRID 880345Notes

Reaction equation

HRID 880345 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2]1.CCN(CC)CC.[CH3:20][C:21](OC(C)=O)=[O:22]>C(Cl)Cl>[C:21]([N:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[CH2:2]1)(=[O:22])[CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 15194053-Aminoazetidine, 3-BOC protected

Product 1

HCID 89730082HCID 89730082, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl azetidin-3-ylcarbamate (100 g, 0.58 mol) and Et3N (88 g, 0.87 mol) in DCM (1500 mL) was added Ac2O (59.6 g, 0.88 mol) dropwise at 0° C. The mixture was then stirred at 0° C. for 2 h, at which time TLC showed the completion of the reaction. The reaction was quenched by addition of water (1000 mL) and then stirred at 20° C. for 30 min. The organic phase was separated, dried (Na2SO4) and concentrated to give the crude product. Seven batches were run in parallel and produced a combined crude product weight of 530 g. This crude was used in next step without the further purification. LCMS (m/z): 215.1 (M+1).

Workup

  1. customthe completion of the reaction
  2. customThe reaction was quenched by addition of water (1000 mL)
  3. stirringstirred at 20° C. for 30 min
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give the crude product

Sources & evidence

ORD record
ord-7e860445944d4175b3aa821704ad24e1
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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