Ethylene Glycol → HCID 24802594, compound

HRID 1786715Notes

Reaction equation

HRID 1786715 reaction equation
C(N(CC)CC)C.ClC([O:11][CH2:12][CH3:13])=O.[Cl:14][C@H:15]1[C@H:19]([CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C@@H:18]([CH2:29][O:30][C:31]2[CH:36]=[C:35]([Cl:37])[CH:34]=[C:33]([Cl:38])[CH:32]=2)[C@H:17]([OH:39])[CH2:16]1.C(O)CO>C(Cl)Cl>[OH:11][CH2:12][CH2:13][O:27][C:26](=[O:28])[CH2:25][CH2:24][CH2:23]/[CH:22]=[CH:21]\[CH2:20][C@H:19]1[C@H:15]([Cl:14])[CH2:16][C@@H:17]([OH:39])[C@@H:18]1[CH2:29][O:30][C:31]1[CH:32]=[C:33]([Cl:38])[CH:34]=[C:35]([Cl:37])[CH:36]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 11502693HCID 11502693, compound

Product 1

HCID 24802594HCID 24802594, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (15 μL, 0.11 mmol) and ethyl chloroformate (15 μL, 0.16 mmol) were added sequentially to a solution of (Z)-7-[(1R,2S,3R,5R)-5-chloro-2-(3,5-dichloro-phenoxymethyl)-3-hydroxy-cyclopentyl]-hept-5-enoic acid (U.S. Provisional Patent Application No. 60/644,069, filed on Jan. 14, 2005, incorporated by reference herein, 10.5 mg, 0.025 mmol) in CH2Cl2 (0.2 mL) at room temperature. After 2.5 h, triethylamine (15 μL, 0.11 mmol) and ethylene glycol (200 μL, 3.59 mmol) were added. After stirring overnight at room temperature, the reaction mixture was partitioned between H2O (5 mL) and CH2Cl2 (5 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×5 mL). The combined organic phase was washed with 1 N HCl (5 mL) then dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (10% MeOH/CH2Cl2) afforded 2.5 mg (22%) of the title compound (1).

Workup

  1. customat room temperature
  2. customthe reaction mixture was partitioned between H2O (5 mL) and CH2Cl2 (5 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (2×5 mL)
  5. washThe combined organic phase was washed with 1 N HCl (5 mL)
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by flash column chromatography on silica gel (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-03b8a4bd98cb48cebc60c1aa63086a6b
Source dataset
uspto-grants-2009_03
Patent number
US07507817B2

Reaction notes

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