Triethylamine → HCID 131730880, compound

HRID 1034561Notes

Reaction equation

HRID 1034561 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=O)[C@@H:10]([CH3:12])[OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH2:17]([O:19][C:20](=[O:23])[CH2:21][NH2:22])[CH3:18].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=NNC=2C=CC=1>ClCCl>[NH:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C@H:9]([C:13]([NH:22][CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:23])=[O:15])[C@@H:10]([CH3:12])[OH:11]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 2724766N-tert-Butoxycarbonyl-L-threonineHCID 178418300HCID 178418300, compound

Product 1

HCID 131730880HCID 131730880, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-threonine (produced by Wako Pure Chemical Industries Ltd.) (11.0 g, 50 mmol) and glycine ethyl ester hydrochloride (produced by Wako Pure Chemical Industries Ltd.) (8.4 g, 60 mmol) were dissolved in dichloromethane (250 mL). After triethylamine (8.4 mL, 60 mmol), N,N′-dicyclohexylcarbodiimide (DCC, 12.4 g, 60 mmol) and hydroxybenzotriazole (9.2 g, 60 mmol) were further added thereto, the mixture was reacted at room temperature for overnight with stirring. After completion of the reaction, reaction mixture was filtered, and then the filtrate was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the product was crystallized from hexane, to obtain Boc-Thr-Gly-OEt (1) (13.0 g) (yield; 85.1%).

Workup

  1. customthe mixture was reacted at room temperature for overnight
  2. customAfter completion of the reaction, reaction mixture
  3. filtrationwas filtered
  4. extractionthe filtrate was extracted with ethyl acetate
  5. concentrationThe extract was concentrated under reduced pressure
  6. customthe product was crystallized from hexane

Sources & evidence

ORD record
ord-925a704b3637401baa0a658294062243
Source dataset
uspto-grants-2013_10
Patent number
US08546072B2

Reaction notes

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