Triethylamine → HCID 24991756, compound

HRID 1786716Notes

Reaction equation

HRID 1786716 reaction equation
C(N(CC)CC)C.ClC(OCC)=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.O[CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>C(Cl)Cl>[N:43]1([CH2:42][CH2:41][O:27][C:26](=[O:28])[CH2:25][CH2:24][CH2:23]/[CH:22]=[CH:21]\[CH2:20][C@H:19]2[C@H:15]([Cl:14])[CH2:16][C@@H:17]([OH:39])[C@@H:18]2[CH2:29][O:30][C:31]2[CH:32]=[C:33]([Cl:38])[CH:34]=[C:35]([Cl:37])[CH:36]=2)[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 611632-MorpholinoethanolHCID 11502693HCID 11502693, compound

Product 1

HCID 24991756HCID 24991756, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (6.5 μL, 0.047 mmol) and ethyl chloroformate (7 μL, 0.073 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 (see U.S. 60/644,069, 20 mg, 0.047 mmol) in CH2Cl2 (0.47 mL) at room temperature. After 2.5 h, triethylamine (6.5 μL, 0.047 mmol) and 4-(2-hydroxyethyl)-morpholine (58 μL, 0.47 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 (5% MeOH/CH2Cl2) afforded 5.1 mg (20%) of the title compound (2).

Workup

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

Sources & evidence

ORD record
ord-9cab839b31194353a02ded500c33c0b4
Source dataset
uspto-grants-2009_03
Patent number
US07507817B2

Reaction notes

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