N,N-dimethylhydroxylamine hydrochloride → HCID 67422874, compound

HRID 1920800Notes

Reaction equation

HRID 1920800 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([C:21]([OH:23])=O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)O.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=C[C:55]=2N=N1.[C:61](=[O:64])([O-])O.[Na+]>ClCCl.O>[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[C@H:11]([C:21]([CH2:55][O:64][CH3:61])=[O:23])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11860409Boc-Hyp(Bzl)-OH

Product 1

HCID 67422874HCID 67422874, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)-L-proline (6.43 g, 20.0 mmol), dimethylhydroxylamine hydrochloride (2.34 g, 24.0 mmol), and diisopropylethylamine (4.18 mL, 24.0 mmol) in dichloromethane (65 mL) was added with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (4.60 g, 24.0 mmol) and 1-hydroxybenzotriazole hydrate (3.68 g, 24.0 mmol) under ice cooling and stirred at room temperature for 16 hours. The reaction solution was added with saturated aqueous sodium hydrogen carbonate solution (10 mL) and water (50 mL) for quenching followed by extraction with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=45/55) to give the title compound as a colorless oily substance (7.15 g, yield 98%).

Workup

  1. customfor quenching
  2. extractionfollowed by extraction with dichloromethane
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=45/55)

Sources & evidence

ORD record
ord-1b7b63b7d86a49e282e39e13e394844f
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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