(2S)-2-amino-5-(((tert-butoxy)carbonyl)amino)pentanoic acid → HCID 89545074, compound

HRID 630657

Reaction equation

HRID 630657 reaction equation
[CH2:1]([O:4][C:5](=[O:35])[C@H:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](OC2C=CC([N+]([O-])=O)=CC=2)=[O:24])=[CH:18][CH:17]=1)[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:2]=[CH2:3].[C:36]([O:40][C:41]([NH:43][CH2:44][CH2:45][CH2:46][C@@H:47]([C:49]([OH:51])=[O:50])[NH2:48])=[O:42])([CH3:39])([CH3:38])[CH3:37]>ClCCl>[CH2:1]([O:4][C:5](=[O:35])[C@@H:6]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([NH:48][C@H:47]([C:49]([OH:51])=[O:50])[CH2:46][CH2:45][CH2:44][NH:43][C:41]([O:40][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:42])=[O:24])=[CH:18][CH:17]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6993436(2S)-2-amino-5-(((tert-butoxy)carbonyl)amino)pentanoic acidHCID 117612078HCID 117612078, compound

Product 1

HCID 89545074HCID 89545074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

3.00 g (6.16 mmol) of the compound from example 1A was dissolved in 60 ml dichloromethane. 1.43 g (6.16 mmol) N5-(tert-Butoxycarbonyl)-L-ornithine was added. The reaction mixture was split into 3 portions. The portions were heated for 30 min in a sealed tube at 75° C. in a microwave synthesizer. The combined reaction mixture was extracted with approx. 500 ml saturated ammonium chloride solution. The aqueous phase was twice back extracted with approx. 30 ml dichloromethane each. The combined organic phases were extracted with approx. 50 ml brine and dried over sodium sulfate. The solvent was removed under reduced pressure. The raw product was dissolved in dichloromethane and chromatographed over approx. 500 ml silica gel. Solvents used were dichloromethane, dichloromethane/methanol 20/1 to dichloromethane/methanol 1/1. The product-containing fractions were combined and concentrated to dryness under reduced pressure. This gave 2.29 g (3.50 mmol, 57% of theory, 89% purity) of the desired product.

Workup

  1. customThe reaction mixture was split into 3 portions
  2. customThe combined reaction mixture
  3. extractionwas extracted with approx. 500 ml saturated ammonium chloride solution
  4. extractionThe aqueous phase was twice back extracted with approx. 30 ml dichloromethane each
  5. extractionThe combined organic phases were extracted with approx. 50 ml brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. dissolutionThe raw product was dissolved in dichloromethane
  9. customchromatographed over approx. 500 ml silica gel
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-825d5db757324a8d9ac38bfcd3757466
Source dataset
uspto-grants-2016_04
Patent number
US09315543B2

Linked notes

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