Ethylmorpholine → HCID 12786119, compound

HRID 1155457Notes

Reaction equation

HRID 1155457 reaction equation
[NH:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:2]([C:9]([OH:11])=O)[CH2:3][O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[NH2:44][C@H:45]([C:54]([O:56][CH3:57])=[O:55])[CH2:46][C:47]1[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=1.Cl.C(N1CCOCC1)C>CN(C)C=O>[NH:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:2]([C:9]([NH:44][C@H:45]([C:54]([O:56][CH3:57])=[O:55])[CH2:46][C:47]1[CH:48]=[CH:49][C:50]([OH:53])=[CH:51][CH:52]=1)=[O:11])[CH2:3][O:4][C:5]([CH3:6])([CH3:7])[CH3:8]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 76956Methyl tyrosinate hydrochlorideHCID 7017896Boc-Ser(tBu)-OH

Product 1

HCID 12786119HCID 12786119, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of Boc-Ser(But)-OH (26 g), dicyclohexylcarbodiimide (28.3 g) and 1-hydroxybenzotriazole (18.6 g) in dimethylformamide (200 ml) was stirred at ice-bath temperature for 60 min and at room temperature for 60 min. A solution of H-Tyr-OMe hydrochloride (23.6 g) and N-ethylmorpholine (14.36 ml) in dimethylformamide (160 ml) was added to the above mixture. The resulting mixture was stirred at room temperature overnight and filtered. The filtrate was evaporated and the residue was dissolved in ethyl acetate. The solution was washed with 5% aqueous citric acid, water, saturated sodium bicarbonate solution, water and brine, dried over anhydrous sodium sulfate, and evaporated to give 39 g of Boc-Ser(But)-Tyr-OMe as an amorphous solid. This dipeptide was crystallized from diethyl ether-hexane to a mp of 109°-111° C.; Anal. Calcd for C22H34N2O7 : C, 60.26% H, 7.82% N, 6.39% and Found: C, 60.68% H, 7.87% N, 6.37% and nmr (CDCl3) δ 1.17 (s, 9H), 1.44 (s, 9H) and 3.67 (s, 3H).

Workup

  1. waitat room temperature for 60 min
  2. stirringThe resulting mixture was stirred at room temperature overnight
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe solution was washed with 5% aqueous citric acid, water, saturated sodium bicarbonate solution, water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-d8acc199113745689e6456ff517db199
Source dataset
uspto-grants-1981_11
Patent number
US04301066

Reaction notes

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