1,2-Dichloroethane → HCID 53666453, compound

HRID 636014Notes

Reaction equation

HRID 636014 reaction equation
[CH:1]1([CH2:7][C@H:8]([C@H:12]([OH:16])[CH2:13][CH2:14][CH3:15])[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)CCl.[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:27][NH2:28].Cl>ClCCl>[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:27][NH:28][C:9](=[O:11])[C@H:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C@H:12]([OH:16])[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 54302611HCID 54302611, compound

Product 1

HCID 53666453HCID 53666453, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

(2R,3R)-2-Cyclohexylmethyl-3-hydroxyhexanoic acid (3.00 g, 13.1 mmol) is dissolved in 30 mL of anhydrous dichloromethane. EDC (2.77 g, 14.5 mmol) is added followed by 2-tetrahydropyranyloxyamine (3.08 g, 26.3 mmol). The reaction is stirred at 25° C. for 8 h and is then poured into 200 mL of 1 M hydrochloric acid. The mixture is extracted with two 250-mL portions of dichloromethane. The combined organics are then washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure to afford (2R,3R)-2-cyclohexylmethyl-3-hydroxyhexanoic acid 2-tetrahydropyranyloxyamide as a foam (3.60 g, 84% yield).

Workup

  1. extractionThe mixture is extracted with two 250-mL portions of dichloromethane
  2. washThe combined organics are then washed with saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1bccd935a77f472ca68a6290a93311e3
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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