Hydrochloric Acid → HCID 54559825, compound

HRID 366097Notes

Reaction equation

HRID 366097 reaction equation
[OH-].[Na+].Cl.[C:4]([NH:14][CH2:15][CH2:16][CH2:17][C@H:18]([C:20]([OH:22])=[O:21])[NH2:19])([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[C:23]1([CH:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>C1COCC1>[C:4]([NH:14][CH2:15][CH2:16][CH2:17][C@H:18]([C:20]([OH:22])=[O:21])[NH:19][C:30](=[O:31])[CH:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 746372,2-Diphenylacetyl chlorideHCID 69885572(2R)-2-amino-5-[(benzyloxy)carbonyl]aminopentanoic acid hydrochloride

Product 1

HCID 54559825HCID 54559825, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 N NaOH (75 mL) was added to a stirred suspension of (R)-N5 -(Cbz)-ornithine hydrochloride (7.5 g; 25 mmol) in THF (114 mL). Once the starting material had dissolved, diphenylacetyl chloride (6.7 g; 26.3 mmol) was added. The reaction was stirred for 3 h at room temperature, then made acidic with cold 1 N HCl and extracted with EtOAc (3×75 mL). The EtOAc extract was washed with brine, dried with Na2SO4, and concentrated to afford the crude product. Purification by flash chromatography on silica eluting with EtOAc:hexanes (1:1) afforded the sub-title compound (10.5 g; 91%).

Workup

  1. dissolutionOnce the starting material had dissolved
  2. extractionextracted with EtOAc (3×75 mL)
  3. extractionThe EtOAc extract
  4. washwas washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by flash chromatography on silica eluting with EtOAc:hexanes (1:1)

Sources & evidence

ORD record
ord-17a7b31f36c146a3a93a681869d39f9a
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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