Hydrochloric Acid → HCID 10970310, compound

HRID 636016Notes

Reaction equation

HRID 636016 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C@@H:9]([CH2:21][CH2:22][CH3:23])[C@@H:10]([CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:11]([OH:13])=[O:12].[C:24](OC=O)(=[O:26])C.Cl>N1C=CC=CC=1>[CH:24]([N:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[C@@H:9]([CH2:21][CH2:22][CH3:23])[C@@H:10]([CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:11]([OH:13])=[O:12])=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 75269Acetic-formic anhydrideHCID 56992436HCID 56992436, compound

Product 1

HCID 10970310HCID 10970310, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(2R,3S)-3-(2-Tetrahydropyranyloxyamino)-2-(cyclohexylmethyl)hexanoic acid (2.00 g, 6.11 mmol) is dissolved in 15 mL of pyridine. Formic acetic anhydride (1.08 mL, 12.2 mmol) is added at 25° C. The reaction is stirred for an additional 6 h and then is poured into 50 mL of cold 1 M hydrochloric acid. The organics are extracted with two 250-mL portions of dichloromethane. The combined organic phases are then washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated in vacuo to afford (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(cyclohexylmethyl)hexanoic acid (2.17 g, 100% yield). APCI-MS m/z 378 (M+Na)+, 354 (M−H)−.

Workup

  1. extractionThe organics are extracted with two 250-mL portions of dichloromethane
  2. washThe combined organic phases are then washed with saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ef47d96fc824ec6964c6db85bd78950
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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