HCID 17851043, compound → HCID 54030461, compound

HRID 1765985Notes

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]>O.[OH-].[Na+].[Co](Cl)Cl>[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]

Participants

Conditions

Temperature: 37 °C

Procedure

In a mixture of water (36.5 ml) and 1N sodium hydroxide solution (29 ml) was dissolved N-acetyl-3-methoxy-4-methyl-DL-phenylalanine (7.28 g). Cobalt chloride (II) hexahydrate (36.5 mg) and acylase (Acylase Amano 36.5 mg) were added to the solution and the mixture was stirred at 37° C. for 15.5 hours while adjusting pH of the reaction mixture to 7.5 with 1N sodium hydroxide solution. Insoluble matters were removed by filtration and pH of the filtrate was adjusted to 3 with 6N hydrochloric acid. After extraction with ethyl acetate, the extract was washed with water, dried over sodium sulfate and the solvent was evaporated under vacuum to give crude N-acetyl-3-methoxy-4-methyl-D-phenylalanine (3.17 g). The crude product was subjected again to the acylase reaction (15.2 mg cobalt chloride (II) hexahydrate, 152 mg acylase, 37° C., pH 7.5, 20 hours) to give pure N-acetyl-3-methoxy-4-methyl-D-phenylalanine (2.70 g) in the form of a viscous oily substance.

Workup

customInsoluble matters were removed by filtration and pH of the filtrate
extractionAfter extraction with ethyl acetate
washthe extract was washed with water
dry with materialdried over sodium sulfate
customthe solvent was evaporated under vacuum
customto give crude N-acetyl-3-methoxy-4-methyl-D-phenylalanine (3.17 g)

Sources & evidence

ORD record: ord-29ce840310b54b7aa04277168bdd53ea
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229992B2

Reaction notes

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