Hydrochloric Acid → HCID 140376918, compound

HRID 1899776Notes

Reaction equation

HRID 1899776 reaction equation
I.[C:2]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][C@@H:10]([C:19]([OH:21])=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].[OH-].[Na+].[CH2:26]([O:33][C:34](Cl)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>O1CCCC1.O.C(OCC)C>[CH2:26]([O:33][C:34]([NH:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][C@@H:10]([C:19]([OH:21])=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:22][CH:23]=1)=[NH:3])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 70049487HCID 70049487, compound

Product 1

HCID 140376918HCID 140376918, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-amidino-N-t-butoxycarbonyl-L-phenylalanine hydroiodide (1.00 g), 4N sodium hydroxide aqueous solution (1.15 ml), tetrahydrofuran (2 ml), and water (10 ml), a solution of benzyloxycarbonyl chloride in tetrahydrofuran (2 ml) was added, being adjusted to pH=12~12.5 with 4N sodium hydroxide aqueous solution. The reaction mixture was diluted with water and diethyl ether, and the separated aqueous layer was neutralized with 10% hydrochloric acid and extracted with ethyl acetate, and washed with water and brine, and dried over magnesium sulfate. After evaporation in vacuo, the resulting precipitate was collected by filtration and washed with diethyl ether to give 4-(N-benzyloxycarbonylamidino)-N-t-butoxycarbonyl-L-phenylalanine (0.53 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation in vacuo
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-718b666cf27444eb830f0ecb2e76a375
Source dataset
uspto-grants-1996_11
Patent number
US05574016

Reaction notes

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