Acetic-formic anhydride → HCID 86756215, compound

HRID 565256Notes

Reaction equation

HRID 565256 reaction equation
C1(CCCCC[C@H:12]([C@@H:16]([NH:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH3:17])[C:13]([OH:15])=[O:14])C=CC=CC=1.[C:26](OC=O)(=[O:28])C>N1C=CC=CC=1>[CH:26]([N:18]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[CH:16]([CH3:17])[CH2:12][C:13]([OH:15])=[O:14])=[O:28]

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 57168074HCID 57168074, compound

Product 1

HCID 86756215HCID 86756215, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (2R,3S)-2-(5-phenyl-1-pentyl)-3-(2-tetrahydropyranyloxyamino)butanoic acid (105 mg, 0.30 mmol) in pyridine (1.5 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-(5-phenyl-1-pentyl)-1-propyl)-3-(formyl-2-tetrahydropyranyloxyamino)butanoic acid as an oil (105 mg, 92% 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-d322d6f2586f409d9b65194773985cfb
Source dataset
uspto-grants-2001_01
Patent number
US06172064B2

Reaction notes

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