Triethylamine → HCID 53852682, compound

HRID 1956694Notes

Reaction equation

HRID 1956694 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:33]([O:40][C:41](Cl)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[NH4+].[Cl-]>ClCCl.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:10][N:11]([C:41]([O:40][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:42])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 25517Ammonium ChlorideHCID 54004440HCID 54004440, compound

Product 1

HCID 53852682HCID 53852682, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the amine from Step D (754 mg, 1.93 mmol) and triethylamine (0.403 mL, 2.89 mmol) in 5 mL of dichloromethane at 0° C. was added benzylchloroformate (0.303 mL, 2.12 mmol). After 2 hours, the solution was poured into EtOAc and sat NH4Cl solution, and the organic layer was washed with sat. NaHCO3 soln. and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product which was purified by silica gel chromatography (30-40% EtOAc/hexane) to obtain the titled compound (360 mg) as a white foam.

Workup

  1. washthe organic layer was washed with sat. NaHCO3 soln
  2. dry with materialand brine, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide the crude product which
  6. customwas purified by silica gel chromatography (30-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-167855cd12df4faaa5453cb803753bb9
Source dataset
uspto-grants-1998_07
Patent number
US05780492

Reaction notes

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