Acetic-formic anhydride → HCID 11245009, compound

HRID 2269343Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@@H:14]([NH:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH3:15])[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24](OC=O)(=[O:26])C>N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@@H:14]([N:16]([CH:24]=[O:26])[O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH3:15])[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (2R,3S)-2-(3-phenyl-1-propyl)-3-(2-tetrahydropyranyloxyamino)butanoic acid (21.4 g, 66.7 mmol) in pyridine (100 mL) at 0° C. is added formic acetic anhydride (30 mL). The resulting solution is allowed to warm to 25° C., stirred for 6 h, and then concentrated to dryness under reduced pressure. The resulting gum is dissolved in EtOAc (300 mL) and washed sequentially with 1 N hydrochloric acid (200 mL) and saturated aqueous sodium chloride solution. The organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure providing (2R,3S)-2-(3-phenyl-1-propyl)-3-(formyl-2-tetrahydropyranyloxyamino)butanoic acid as an oil (18.9 g, 81% yield). ESI-MS m/z 372 (M+Na)+348 (M−1)31 .

Workup

concentrationconcentrated to dryness under reduced pressure
dissolutionThe resulting gum is dissolved in EtOAc (300 mL)
washwashed sequentially with 1 N hydrochloric acid (200 mL) and saturated aqueous sodium chloride solution
dry with materialThe organic layer is dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c4dcdb04caaf45a3a3e81cdb94d2e6f8
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329400B1

Reaction notes

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