Sodium Hydroxide → HCID 54030461, compound

HRID 1374982Notes

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]

Participants

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

customThe insoluble material was removed by filtration
extractionextracted with ethyl acetate
washwashed with water
dry with materialdried over sodium sulfate
customevaporated in vacuo
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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