Diethylamine → HCID 67321271, compound

HRID 1023014Notes

Reaction equation

HRID 1023014 reaction equation
C[N:2]([C@@H:19]1[CH2:34][C:33]2=[CH:35][CH:36]=[C:30]([CH:31]=[CH:32]2)[O:29][CH2:28][CH:27]=[CH:26][CH2:25][O:24][CH2:23][C@H:22]([CH:37]([CH3:39])[CH3:38])[NH:21][C:20]1=[O:40])C(=O)OC1C2C=CC=CC=2C2C1=CC=CC=2.C(NCC)C>ClCCl>[NH2:2][C@@H:19]1[CH2:34][C:33]2=[CH:32][CH:31]=[C:30]([CH:36]=[CH:35]2)[O:29][CH2:28][CH:27]=[CH:26][CH2:25][O:24][CH2:23][C@H:22]([CH:37]([CH3:38])[CH3:39])[NH:21][C:20]1=[O:40]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 67320233HCID 67320233, compound

Product 1

HCID 67321271HCID 67321271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.66 g (6.78 mmol) of 9H-fluoren-9-yl methyl((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),4,14(18),15-tetraen-12-yl)carbamate (1-1D) in 300 ml of dichloromethane was mixed with 75 ml of diethylamine and stirred at RT for 5 h. The mixture was concentrated and purified by preparative HPLC. Acetonitrile was removed from the combined product fractions in a rotary evaporator, saturated NaHCO3 solution was added, and the mixture was extracted twice with ethyl acetate, saturated with sodium chloride and again extracted with ethyl acetate. The combined ethyl acetate phases were dried over Na2SO4, filtered and concentrated. The resulting substance was pure enough for further reactions.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC
  3. customAcetonitrile was removed from the combined product fractions in a rotary evaporator, saturated NaHCO3 solution
  4. additionwas added
  5. extractionthe mixture was extracted twice with ethyl acetate, saturated with sodium chloride
  6. extractionagain extracted with ethyl acetate
  7. dry with materialThe combined ethyl acetate phases were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-72c568ad56ca4229bb8e44e7c19e0e3e
Source dataset
uspto-grants-2014_05
Patent number
US08722655B2

Reaction notes

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