Diethyl Ether → HCID 71133735, compound

HRID 1523118Notes

Reaction equation

HRID 1523118 reaction equation
[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][N:19]([CH3:23])[CH2:18][CH2:17][N:16]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[CH2:15][CH2:14][CH2:13][N:12]([CH3:32])[CH2:11][CH2:10]1)([O:3]C(C)(C)C)=[O:2].CCOCC>C(C(O)=O)(F)(F)F.C(Cl)Cl>[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][N:19]([CH3:23])[CH2:18][CH2:17][N:16]([CH2:24][C:25]([OH:27])=[O:26])[CH2:15][CH2:14][CH2:13][N:12]([CH3:32])[CH2:11][CH2:10]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 71133766HCID 71133766, compound

Product 1

HCID 71133735HCID 71133735, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound (33) (1.46 g, 3.19 mmol) was dissolved in a mixture of CF3CO2H (TFA) and CH2Cl2 (1:1 (v/v), 50 ml). The resultant mixture was stirred at an ambient temperature for 24 hours. The solvent was removed under reduced pressure to give an oily residue, which was then treated with Et2O to obtain a white solid of compound (34) (1.09 g, 99% yield). HRMS (FAB) calculated for C16H33N4O4: 345.2502 [(M+H)+], measured value: 345.2506 [(M+H)+].

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give an oily residue, which

Sources & evidence

ORD record
ord-3ddfbaec50e24ade873ffbdaf9a489ca
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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