Triethylamine → HCID 10022430, compound

HRID 2118634Notes

Reaction equation

HRID 2118634 reaction equation
[C:1]([NH:8][C@@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:18][O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH:24]([CH3:26])[CH3:25])[NH2:22].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:18][O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH:24]([CH3:26])[CH3:25])[NH:22][C:14](=[O:16])[C@@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 111051N-(tert-Butyloxycarbonyl)-D-methionineHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 10022430HCID 10022430, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boc-D-methionine (34.2 g, 0.137 mole) and L-leucine methylester hydrochloride (25.0 g, 0.137 mole) was dissolved in 450 ml of methylene chloride and triethylamine (19.15 ml, 13.9 g, 0.137 mole) was added. Dicyclohexylcarbodiimide (62 ml of a 0.5 g/ml solution in CH2Cl2, 0.15 mole) was then added followed by stirring at room temperature overnight. The mixture was filtered and the filtrate was extracted with three 150 ml portions of dilute citric acid and three 150 ml portions of 1N sodium biocarbonate. After drying with sodium sulfate, the solution was concentrated in vacuo. Chromatography of the crude material on silica gel eluting with ethyl acetate-hexane (1:1; 2:1) followed by ethyl acetate gave pure product which crystallized from ethyl acetate-hexane to give 28.4 g of product (53%), m.p. 61°-64°. The nmr spectrum was consistent with the expected structure.

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe filtrate was extracted with three 150 ml portions of dilute citric acid and three 150 ml portions of 1N sodium biocarbonate
  3. dry with materialAfter drying with sodium sulfate
  4. concentrationthe solution was concentrated in vacuo
  5. customgave pure product which
  6. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5a814dac83d5420290490822b000e36b
Source dataset
uspto-grants-1987_07
Patent number
US04680283

Reaction notes

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