1,2-Dichloroethane → HCID 54553173, compound

HRID 2269367Notes

Reaction equation

HRID 2269367 reaction equation
[CH2:1]([C@H:4]([C@H:8]([OH:10])[CH3:9])[C:5]([OH:7])=O)[C:2]#[CH:3].[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][NH2:18].C(Cl)CCl>ClCCl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][NH:18][C:5](=[O:7])[C@H:4]([CH2:1][C:2]#[CH:3])[C@H:8]([OH:10])[CH3:9]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 54154673HCID 54154673, compound

Product 1

HCID 54553173HCID 54553173, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

To a solution of (2R,3R)-2-(2-propyne-1-yl)-3-hydroxybutanoic acid (3.0 g, 21.13 mmol) in dichloromethane (50 mL) is added 2-tetrahydropyranyloxyamine (3.0 g, 25.35 mmol) and EDC (4.5 g, 23.24 mmol). The resulting solution is stirred at 23° C. for 4 h, then diluted with dichloromethane (100 mL) and washed with 1 M hydrochloric acid. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (2R,3R)-2-(2-propyne-1-yl)-3-hydroxybutanoic acid 2-tetrahydropyranyloxyamide as a foam (1.9 g, 37% yield). 1H NMR (400 MHz, CDCl3) δ 8.82 (bs, 1H), 4.96 (m, 1H), 3.94 (m, 2H), 3.62 (m, 1H), 2.64 (m, 1H), 2.56 (m, 1H), 2.23 (m, 1H), 2.04 (m, 1H), 1.82 (m, 2H), 1.61 (m, 4H), 1.23 (d, 3H) ppm. ESI-MS m/z 240.4 (M−H)−.

Workup

  1. washwashed with 1 M hydrochloric acid
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4a7ee1c2a1d43dd972208e65718c2f2
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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