Triethylamine → HCID 10315872, compound

HRID 2231379Notes

Reaction equation

HRID 2231379 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([O:19]C1C(F)=C(F)C(F)=C(F)C=1F)=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(N(CC)CC)C>O1CCOCC1.C(OCC)(=O)C>[C:6]([NH:8][C@H:9]([C:17]([NH:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12176Glycine ethyl esterHCID 10993711pentafluorophenyl N-t-butyloxycarbonyl-L-phenylalaninate

Product 1

HCID 10315872HCID 10315872, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.86 g (2 mmol) of pentafluorophenyl N-t-butyloxycarbonyl-L-phenylalaninate, prepared according to Example 48, in 10 ml of dioxane, 0.28 g (2.2 mmol) of ethyl glycinate (hydrochloride) and 0.31 g (3 mmol) of triethylamine are added simultaneously. The mixture is stirred for one hour at room temperature. It is diluted with 10 ml of ethyl acetate and washed with aqueous 0.1N hydrochloric acid, potassium bicarbonate and sodium chloride solutions. The organic phase is dried over magnesium sulphate and evaporated. The residue is taken up with a 4:6 ethyl acetate/hexane mixture and filtered on silica. After evaporation, 0.53 g (Y=76%) of BOC-Phe-Gly-OEt is obtained.

Workup

  1. washwashed with aqueous 0.1N hydrochloric acid, potassium bicarbonate and sodium chloride solutions
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. customevaporated
  4. filtrationfiltered on silica
  5. customAfter evaporation

Sources & evidence

ORD record
ord-8dd67861dc3c4d649f34ee3ba7370d13
Source dataset
uspto-grants-1988_11
Patent number
US04782164

Reaction notes

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