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Sodium Hydroxide → HCID 54030461, compound

HRID 1374982
Notes
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Reaction equation

HRID 1374982 reaction equation
[C:1]([NH:4][CH:5]([C:16]([OH:18])=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([O:14][CH3:15])[CH:8]=1)(=[O:3])[CH3:2].[OH-].[Na+]>O.O.O.O.O.O.[Co](Cl)Cl.O>[C:1]([NH:4][C@@H:5]([C:16]([OH:18])=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([O:14][CH3:15])[CH:8]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 17851043HCID 17851043, compound

Product 1

HCID 54030461HCID 54030461, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalyst2×HCID 962WaterSolvent

Conditions

Temperature
37 °C

Procedure

N-Acetyl-3-methoxy-4-methyl-DL-phenylalanine (7.28 g) was dissolved into a mixture of water (36.5 ml) and 1N sodium hydroxide solution (29 ml). Cobalt(II) chloride hexahydrate (36.5 mg) and acylase (Acylase Amano, 365 mg) were added to the solution and the mixture was stirred at 37° C. for 15.5 hours with controlling the pH of the reaction mixture to 7.5 with 1N sodium hydroxide solution. The insoluble material was removed by filtration and the pH of the filtrate was made to 3 with 6N hydrochloric acid, extracted with ethyl acetate, washed with water, dried over sodium sulfate, and evaporated in vacuo to give crude N-acetyl-3-methoxy-4-methyl-D-phenylalanine (3.17 g). The crude product was again subjected to the acylase reaction (cobalt(II) chloride hexahydrate 15.2 mg, acylase 152 mg, 37° C., pH 7.5, 20 hours) to give pure N-acetyl-3-methoxy-4-methyl-D-phenylalanine (2.70 g) as a viscous oil.

Workup

  1. customThe insoluble material was removed by filtration
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customto give crude N-acetyl-3-methoxy-4-methyl-D-phenylalanine (3.17 g)

Sources & evidence

ORD record
ord-164a05fad17d42558ce0e3a148c498c9
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07166598B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes