Diglycolamine → HCID 57357491, compound

HRID 1836083Notes

Reaction equation

HRID 1836083 reaction equation
C(O[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(C)(C)C.[NH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19]>C(Cl)(Cl)Cl>[C:6]([CH:14]([NH2:13])[CH2:15][O:16][CH2:17][CH2:18][OH:19])([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12]

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 57357491HCID 57357491, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

This compound was prepared by a modification of the procedure described by, Lebeau, L, et al., “Synthesis of New Phospholipids Linked to Steroid-Hormone Derivatives Designed for Two-Dimensional Crystallization of Proteins,” Helv. Chim. Acta 1991, 74, 1697-1706, the contents of which are incorporated herein by reference. A solution of di-tert-butylcarbonate (10.27 g, 47.2 mmol) in chloroform (40 mL) was added to a solution of 2-(2-aminoethoxy)-ethanol (1, 5.0 g, 47.62 mmol) in chloroform (40 mL) and the mixture was stirred at room temperature for 1.5 hours. The solution was washed with water (30 mL) and the organic layer was dried over anhydrous MgSO4 and concentrated in vacuo to give the product (9.6 g, 99%): 1H NMR δ1.45(s, 9H, t-Bu), 3.32 (m, 2H, NHCH2), 3.43 (bs, 1H, OH), 3.56 (m, 4H, CH2OCH2), 3.73 (t, 2H, J=5.4, CH2OH), 5.43 (bs, 1H, NH); 13C NMR δ28.21 40.21, 61.31, 70.08, 72.14, 77.18, 79.06, 156.06.

Workup

  1. customThis compound was prepared by a modification of the procedure
  2. customLinked to Steroid-Hormone Derivatives Designed for Two-Dimensional Crystallization of Proteins,” Helv
  3. washThe solution was washed with water (30 mL)
  4. dry with materialthe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbdebc60a9c64ed2b4ef32bd622d842c
Source dataset
uspto-grants-2004_08
Patent number
US06777387B2

Reaction notes

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