1,2-Dichloroethane → HCID 53943221, compound

HRID 636020Notes

Reaction equation

HRID 636020 reaction equation
[CH3:1][CH:2]([CH3:11])[CH2:3][C@H:4]([C@H:8]([OH:10])[CH3:9])[C:5]([OH:7])=O.[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][NH2:19].[CH2:20](Cl)[CH2:21]Cl>ClCCl>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][NH:19][C:5](=[O:7])[C@H:4]([CH2:3][CH:2]([CH3:1])[CH3:11])[C@H:8]([OH:10])[CH2:9][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 53655744HCID 53655744, compound

Product 1

HCID 53943221HCID 53943221, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R,3R)-2-(2-Methyl-1-propyl)-3-hydroxybutanoic acid (6.6 g, 41.2 mmol) and 5.3 g (45.3 mmol) of 2-tetrahydropyranyloxyamine are stirred in 60 mL of dichloromethane as 8.7 g (45.3 mmol) of EDC is added. After 4 h at 25° C. the reaction mixture is partitioned between 1 N aqueous hydrochloric acid and dichloromethane and the organics are washed with saturated aqueous sodium bicarbonate. The organics are dried over magnesium sulfate and concentrated under reduced pressure to afford 5.9 g (55%) of (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxyhexanoic acid 2-tetrahydropyranyloxyamide as an oil.

Workup

  1. additionis added
  2. customAfter 4 h at 25° C. the reaction mixture is partitioned between 1 N aqueous hydrochloric acid and dichloromethane
  3. washthe organics are washed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organics are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63eb5a1fe05f4b91a5a7e06d18d8eb55
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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