Acetic-formic anhydride → HCID 57140699, compound

HRID 565254Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C@H:11]([C@@H:15]([NH:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH3:16])[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[C:25](OC=O)(=[O:27])C>N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C@H:11]([C@@H:15]([N:17]([CH:25]=[O:27])[O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH3:16])[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (2R,3S)-2-(3-(4-methylphenyl)-1-propyl)-3-(2-tetrahydropyranyloxyamino)butanoic acid (114 mg, 0.34 mmol) in pyridine (2 mL) at 0° C. is added formic acetic anhydride (0.3 mL). The resulting solution is allowed to warm to 25° C., stirred for 3 h, and then concentrated to dryness under reduced pressure. The resulting gum is dissolved in ethyl acetate (30 mL) and washed sequentially with 1 M hydrochloric acid (20 mL) and saturated aqueous sodium chloride solution. The organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (2R,3S)-2-(3-(4-methylphenyl)-1-propyl)-3-(formyl-2-tetrahydropyranyloxyamino)butanoic acid as an oil (120 mg, 97% yield).

Workup

concentrationconcentrated to dryness under reduced pressure
dissolutionThe resulting gum is dissolved in ethyl acetate (30 mL)
washwashed sequentially with 1 M hydrochloric acid (20 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-941552b4fea04a4a95a280a0c366b87a
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172064B2

Reaction notes

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