Triethylamine → HCID 53986628, compound

HRID 2418518Notes

Reaction equation

HRID 2418518 reaction equation
Cl.COC(=O)[C@@H]1CCCN1.[CH3:11][O:12][C:13](=[O:30])[C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(N(CC)CC)C.C(OC(NCC(O)=O)=O)(C)(C)C.CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl>[CH3:11][O:12][C:13](=[O:30])[C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70486501HCID 70486501, compound

Product 1

HCID 53986628HCID 53986628, compoundYield 261.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-t-Butyloxycarbonyl-glycyl-L-proline methylester L-proline methylester hydrochloride (13.6 g, 82.7 m mole) was suspended in chloroform (200 ml) and to the suspended solution triethylamine (8.3 g, 82.7 m mole) was added while cooling. To the solution, N-t-butyloxycarbonyl glycine (14.5 g, 82.7 m mole) was added and WSC hydrochloride (15.82 g, 82.7 m mole) was gradually added thereto while cooling with ice. The reaction was carried out for 2 hours while cooling with ice, and next overnight at room temperature. The reaction solution was washed with 10% citric acid, aqueous sodium chloride, 5% sodium bicarbonate and aqueous sodium chloride in order, and dried with anhydrous sodium sulfate. The solution was distilled under reduced pressure leaving a syrupy N-t-butyloxycarbonyl-glycyl-L-proline methylester product (22.5 g, 78.5 m mole, yield: 95%). This product gave a single spot with Rf =0.48 by silica gel thin layer chromatography (developing solvent, benzene:ethyl acetate=1:1, colour forming method: spraying of 25% hydrobromic acid and 0.1% ninhydrin and heating).

Workup

  1. additionwas added
  2. temperaturewhile cooling
  3. temperaturewhile cooling with ice
  4. washThe reaction solution was washed with 10% citric acid, aqueous sodium chloride, 5% sodium bicarbonate and aqueous sodium chloride in order
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationThe solution was distilled under reduced pressure

Sources & evidence

ORD record
ord-05c53e4c12b24d6aa2840c964c99acf0
Source dataset
uspto-grants-1984_09
Patent number
US04472381

Reaction notes

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