Triethylamine → Z-Ser(But)-Leu-OMe

HRID 1731234Notes

Reaction equation

HRID 1731234 reaction equation
C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[NH:16]([C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[C@H:17]([C:24]([OH:26])=O)[CH2:18][O:19][C:20]([CH3:23])([CH3:22])[CH3:21].[NH2:37][C@H:38]([C:43]([O:45][CH3:46])=[O:44])[CH2:39][CH:40]([CH3:42])[CH3:41].Cl>C(OCC)(=O)C>[NH:16]([C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[C@H:17]([C:24]([NH:37][C@H:38]([C:43]([O:45][CH3:46])=[O:44])[CH2:39][CH:40]([CH3:42])[CH3:41])=[O:26])[CH2:18][O:19][C:20]([CH3:21])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 1715617Z-Ser(tBu)-OHHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 13892395Z-Ser(But)-Leu-OMe

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2.75 ml of triethylamine and 2.63 ml of chloroformic acid isobutyl ester are added to 5.9 g of Z-Ser(But)-OH in 20 ml of ethyl acetate at -10°C. After 10 minutes, 4.0 g of H-Leu-OMe-HCl and 3.05 ml of triethylamine are added. After stirring for 11/2 hours in an ice bath, the mixture is extracted by shaking with phosphoric acid and sodium bicarbonate solution and after drying over sodium sulphate the ethyl acetate is evaporated completely. 8.2 g of a waxy mass are obtained. Melting point (after crystallisation from hexane): 56°-58°C.

Workup

  1. extractionthe mixture is extracted
  2. stirringby shaking with phosphoric acid and sodium bicarbonate solution
  3. dry with materialafter drying over sodium sulphate the ethyl acetate
  4. customis evaporated completely
  5. custom8.2 g of a waxy mass are obtained
  6. customMelting point (after crystallisation from hexane)
  7. custom56°-58°C.

Sources & evidence

ORD record
ord-43c49ebd5c3d43c8ab0b3df30a521619
Source dataset
uspto-grants-1976_11
Patent number
US03994871

Reaction notes

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