Hydrochloric Acid → HCID 86744319, compound

HRID 1089542Notes

Reaction equation

HRID 1089542 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:24]=[C:22]([OH:23])[C:20]([OH:21])=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:27](Cl)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29].Cl>O.C(OCC)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:24]=[C:22]([OH:23])[C:20]([OH:21])=[CH:19][CH:18]=1)[C:13]([O:15][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 148528073-hydroxy-N-[(phenylmethoxy)carbonyl]- L-Tyrosine

Product 1

HCID 86744319HCID 86744319, compoundYield 62.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-benzyloxycarbonyl-L-dopa (3.30 g) was dissolved in a mixture of 50 ml of water and 10 ml of ethyl ether. Under stirring with ice cooling, 10 ml of a 1N sodium hydroxide aqueous solution and 10 ml of an ethyl ether solution of 1.20 g pivaloyl chloride were added dropwise at the same time over a period of 30 minutes while keeping pH at 6.0 to 8.0 After the addition was over, the mixture was stirred at room temperature for 1 hour, and diluted with 50 ml of ethyl acetate. Subsequently, 2N hydrochloric acid was added to adjust pH to 2.0. An organic layer was taken out, water-washed and dried over anhydrous magnesium sulfate. After the drying agent was separated by filtration, the solvent was evaporated under reduced pressure. When the residue was purified by silica gel column chromatography (Wakogel C-100, 120 g, eluted with methylene chloride/methanol=5/1), 2.60 g (yield 62.6%) of N-benzyloxycarbonyl-mono-O-pivaloyl-L-dopa was obtained as a pale yellow glass solid.

Workup

  1. additionwere added dropwise at the same time over a period of 30 minutes
  2. additionAfter the addition
  3. washwater-washed
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the drying agent was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customWhen the residue was purified by silica gel column chromatography (Wakogel C-100, 120 g, eluted with methylene chloride/methanol=5/1)

Sources & evidence

ORD record
ord-21f6621265ec496eb7548ace048cab62
Source dataset
uspto-grants-1990_10
Patent number
US04966915

Reaction notes

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