Triethylamine → Z-Asp(OtBu)-Val-OtBu

HRID 2371371Notes

Reaction equation

HRID 2371371 reaction equation
C(N(CC)CC)C.[NH2:8][C@H:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:10]([CH3:12])[CH3:11].Cl.[NH:21]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:22]([C:31](ON1C(=O)CCC1=O)=[O:32])[CH2:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O>[NH:21]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:22]([C:31]([NH:8][C@H:9]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:32])[CH2:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11026196L-Aspartic acid, N-((phenylmethoxy)carbonyl)-, 4-(1,1-dimethylethyl) 1-(2,5-dioxo-1-pyrrolidinyl) esterHCID 12490702tert-butyl (2S)-2-amino-3-methylbutanoate hydrochloride

Product 1

HCID 70050186Z-Asp(OtBu)-Val-OtBuYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.68 ml (12.0 mmol) of triethylamine are added to a suspension containing 2.58 g (12.0 mmol) of H-Val-OtBu.HCl and 4.62 g (11.0 mmol) of Z-Asp(OtBu)-OSu in 25 ml of dimethylformamide (DMF). The reaction mixture is left to stand overnight, then evaporated under reduced pressure. The residue is mixed with 50 ml of ethyl acetate and the suspension obtained is successively washed with 25 ml of water, 3 times with 25 ml of 1 mol/liter hydrochloric acid each, 3 times with 25 ml of 5% aqueous sodium hydrogenocarbonate each and finally with 25 ml of water, dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain 4.3 g (81.7%) of oily Z-Asp(OtBu)-Val-OtBu protected dipeptide, Rf1 =0.85.

Workup

  1. waitThe reaction mixture is left
  2. customevaporated under reduced pressure
  3. additionThe residue is mixed with 50 ml of ethyl acetate
  4. customthe suspension obtained
  5. washis successively washed with 25 ml of water, 3 times with 25 ml of 1 mol/liter hydrochloric acid each, 3 times with 25 ml of 5% aqueous sodium
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-80e1ff23442740fab22af43a8ce136fb
Source dataset
uspto-grants-1992_03
Patent number
US05093320

Reaction notes

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