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Water → N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-isoleucine (S)-alpha-ethylbenzylamide

HRID 769
Notes
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Reaction equation

HRID 769 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@@H:27]([C:32](O)=[O:33])[C@@H:28]([CH2:30][CH3:31])[CH3:29])=[O:25])[CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14](=[O:16])[OH:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:35]([C@H:37]([NH2:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:36].O.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH2:35]([C@H:37]([NH:44][C:32](=[O:33])[C@@H:27]([C@@H:28]([CH2:30][CH3:31])[CH3:29])[NH:26][C:24](=[O:25])[C@H:12]([CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14](=[O:15])[OH:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 6993773(1S)-1-phenylpropan-1-amineHCID 54543031N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-isoleucine

Product 1

HCID 53679369N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-isoleucine (S)-alpha-ethylbenzylamideYield 33.1%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.69 g (14.2 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine and 2.04 g (15.1 mmols) of (S)-α-ethylbenzylamine in 200 ml of methylene chloride were added 2.73 g (14.2 mmols) of water-soluble carbodiimide hydrochloride and 1.92 g (14.2 mmols) of HOBt under cooling and stirred for one hour under cooling and then overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and 150 ml of ethyl acetate was added. The resulting residue was washed two times each with 70 ml of aqueous 5% citric acid, once with 70 ml of water, two times each with 70 ml of aqueous 5% sodium hydrogencarbonate and once with 70 ml of brine in that order. The resulting organic layer was dried with anhydrous magnesium sulfate, the magnesium sulfate was removed by filtration, and the resulting filtrate was concentrated under reduced pressure. The resulting residue was dissolved in chloroform and concentrated under reduced pressure. The resulting solid residue was washed with ethyl acetate and dried to obtain 2.81 g (4.7 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide.

Workup

  1. temperatureunder cooling
  2. temperatureunder cooling
  3. customovernight
  4. customat room temperature
  5. concentrationThe reaction mixture was concentrated under reduced pressure, and 150 ml of ethyl acetate
  6. additionwas added
  7. washThe resulting residue was washed two times each with 70 ml of aqueous 5% citric acid
  8. dry with materialThe resulting organic layer was dried with anhydrous magnesium sulfate
  9. customthe magnesium sulfate was removed by filtration
  10. concentrationthe resulting filtrate was concentrated under reduced pressure
  11. dissolutionThe resulting residue was dissolved in chloroform
  12. concentrationconcentrated under reduced pressure
  13. washThe resulting solid residue was washed with ethyl acetate
  14. customdried

Sources & evidence

ORD record
ord-a473542e2c91474d920bd8a0505e632c
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723165

Reaction notes

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