Triethylamine → HCID 58564208, compound

HRID 473938Notes

Reaction equation

HRID 473938 reaction equation
ON1[C:6]2C=CC=C[C:5]=2N=N1.C(N(CC)CC)C.[OH:18][NH:19][C:20](=[NH:47])[C:21]1[CH:26]=[CH:25][C:24]([C@@H:27]([N:29]2[CH2:34][CH2:33][C@:32]([CH2:41][C:42]([OH:45])([CH3:44])[CH3:43])([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:31][C:30]2=[O:46])[CH3:28])=[CH:23][CH:22]=1.C(N=C=NCCCN(C)C)C>C(O)C.C(OCC)(=O)C.CN(C)C=O.C(O)(=O)C>[OH:45][C:42]([CH3:44])([CH3:43])[CH2:41][C@@:32]1([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:31][C:30](=[O:46])[N:29]([C@H:27]([C:24]2[CH:23]=[CH:22][C:21]([C:20]3[N:47]=[C:5]([CH3:6])[O:18][N:19]=3)=[CH:26][CH:25]=2)[CH3:28])[CH2:34][CH2:33]1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178461685HCID 178461685, compound

Product 1

HCID 58564208HCID 58564208, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

1-Hydroxybenzotriazole (74 mg), triethylamine (0.11 mL), N-hydroxy-4-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-benzamidine (150 mg), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (140 mg) were added in the given order to a solution of acetic acid (21 μL) and dimethylformamide (3 mL) at room temperature. The resulting mixture was stirred at 70° C. for 1 h and then at room temperature overnight. Ethyl acetate was added and the resulting mixture was washed with water and brine and dried (Na2SO4). The solvent was removed and the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2->94:6) to afford the intermediate which was taken up in ethanol (2 mL) and stirred with microwave irradiation at 120° C. for 30 min. After cooling to room temperature, the solvent was evaporated and the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 97:3) to afford the title compound.

Workup

  1. customat room temperature
  2. customovernight
  3. washthe resulting mixture was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. customthe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2->94:6)
  7. customto afford the intermediate which
  8. stirringstirred with microwave irradiation at 120° C. for 30 min
  9. temperatureAfter cooling to room temperature
  10. customthe solvent was evaporated
  11. customthe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-cfed5844e0f34eba93269c1d5900deb1
Source dataset
uspto-grants-2014_01
Patent number
US08637505B2

Reaction notes

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