Triethylamine → HCID 178473977, compound

HRID 1728494Notes

Reaction equation

HRID 1728494 reaction equation
ClC(OCC)=O.[C:7]([C@@H:10]1[N:13]([C:14](=[O:16])[CH3:15])[C:12](=[O:17])[C@H:11]1[CH2:18][CH2:19][CH2:20][NH:21][C:22]([NH:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])=[N:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])(O)=[O:8].C(N(CC)CC)C.Cl.[CH2:53]([O:60][C:61](=[O:67])[C@@H:62]1[CH2:66][CH2:65][CH2:64][NH:63]1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>C(Cl)Cl>[C:54]1([CH2:53][O:60][C:61]([CH:62]2[CH2:66][CH2:65][CH2:64][N:63]2[C:7]([C@@H:10]2[N:13]([C:14](=[O:16])[CH3:15])[C:12](=[O:17])[C@H:11]2[CH2:18][CH2:19][CH2:20][NH:21][C:22]([NH:34][C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:36])=[N:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[O:8])=[O:67])[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 2733413Proline benzyl ester hydrochlorideHCID 178473979HCID 178473979, compound

Product 1

HCID 178473977HCID 178473977, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a -5° C. methylene chloride (1 mL) solution of ethyl chloroformate (0.12 g, 1.1 mmol) was added a methylene chloride solution of compound 29 (0.35 g, 0.7 mmol), followed by the addition of triethylamine (0.112 g, 1.1 mmol). The resultant reaction mixture was stirred for 1 h between -5° C. and 5° C. Triethylamine (0.11 g, 1.1 mmol) and proline benzylester hydrochloride (260 mg, 1.1 mmol) was added, and the solution was stirred between -5° C. to 5° C. for an additional 15 min and for 16 h at room temperature. The solution was washed with saturated aqueous NaHCO3 solution, dried (MgSO4), and concentrated. The residue was purified by silica gel chromatography (Et2O:EtOAc/8:2) to afford 70 mg (14%) of the title compound.

Workup

  1. customThe resultant reaction mixture
  2. stirringthe solution was stirred between -5° C. to 5° C. for an additional 15 min and for 16 h at room temperature
  3. washThe solution was washed with saturated aqueous NaHCO3 solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (Et2O:EtOAc/8:2)

Sources & evidence

ORD record
ord-e69be9c2b3604cb2967bdc2c11e6ee31
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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