Triethylamine → HCID 68600866, compound

HRID 1185479Notes

Reaction equation

HRID 1185479 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16](=[O:22])[NH:17][CH:18]1[CH2:21][NH:20][CH2:19]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:32]>C(Cl)Cl>[CH2:34]([O:33][C:31]([N:20]1[CH2:21][CH:18]([NH:17][C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:22])[CH2:19]1)=[O:32])[CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 68599591HCID 68599591, compound

Product 1

HCID 68600866HCID 68600866, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2 g of Azetidin-3-yl-carbamic acid benzyl ester trifluoroacetate (prepared by standard protection and deprotection procedures from 3-Amino-azetidine-1-carboxylic acid tert-butyl ester) in 10 ml of DCM, 1.9 g of triethylamine was added and the mixture was cooled to 0° C. Then, 938 mg of butyl chloroformate was slowly added. After the addition was completed the reaction mixture was allowed to warm to RT and to stir for 1 h. Then, 200 ml of DCM was added and the organic phase was washed two times with 0.1M aqueous hydrochloric acid and the with saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 1.4 g.

Workup

  1. additionAfter the addition
  2. temperatureto warm to RT
  3. washthe organic phase was washed two times with 0.1M aqueous hydrochloric acid
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvents were removed under reduced pressure
  6. customThe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  7. additionThe fractions containing the product
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-76d43405866a44a796a6d50962dcec0d
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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