Phenol → HCID 57090268, compound

HRID 404943Notes

Reaction equation

[O:1]([C:8]([NH:10][C@H:11]([C:19]([OH:21])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9])C1C=CC=CC=1.[C:22]1(O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(=O)CC>[C:8]([NH:10][C@H:11]([C:19]([O:21][C:19](=[O:20])[C@H:11]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:10][C:8]([OH:1])=[O:9])=[O:20])[CH2:12][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([OH:9])=[O:1]

Participants

Conditions

Temperature: 80 °C

Procedure

Under a nitrogen atmosphere, a solution prepared by dissolving 571 mg (2 mmol) of N-phenoxycarbonyl-L-phenylalanine and 184 mg (2 mmol) of phenol in 20 mL of 2-butanone was charged into a two-necked round bottom flask having a volume of 100 mL and mounted with a Dimroth condenser, and was then stirred at 80° C. for 8 hours. The fact that N-carboxy-phenylalanine anhydride was obtained in a yield of 99% or more was confirmed by subjecting the reaction mixture to NMR determination.

Workup

customUnder a nitrogen atmosphere, a solution prepared
additionwas charged into a two-necked round bottom flask

Sources & evidence

ORD record: ord-ef3a0fef1c944211b11a0ecf5dcd63b3
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748650B2

Reaction notes

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