Acetic-formic anhydride → HCID 57151785, compound

HRID 565248Notes

Reaction equation

HRID 565248 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][C@H:9]([C@@H:13]([NH:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH3:14])[C:10]([OH:12])=[O:11].[C:23](OC=O)(=[O:25])C>N1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][C@H:9]([C@@H:13]([N:15]([CH:23]=[O:25])[O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH3:14])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 57246922HCID 57246922, compound

Product 1

HCID 57151785HCID 57151785, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (2R,3S)-2-(3-(thiophene-2-yl)-1-propyl)-3-(2-tetrahydropyranyloxyamino)butanoic acid (91 mg, 0.278 mmol) in pyridine (1 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-(thiophene-2-yl)-1-propyl)-3-(formyl-2-tetrahydropyranyloxyamino)butanoic acid as an oil (90 mg, 91% yield).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. dissolutionThe resulting gum is dissolved in ethyl acetate (30 mL)
  3. washwashed sequentially with 1 M hydrochloric acid (20 mL) and saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae68e65aa78f4e9e99b8ab02907b5590
Source dataset
uspto-grants-2001_01
Patent number
US06172064B2

Reaction notes

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