Triethylamine → HCID 69510007, compound

HRID 970258Notes

Reaction equation

HRID 970258 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].C(N([CH2:27][CH3:28])CC)C.[OH:29][C:30]1[CH:49]=[CH:48][C:33]([CH:34]=[CH:35][C:36]([O:38][C@@H:39]2[CH:43]3[O:44][CH2:45][C@@H:46]([OH:47])[CH:42]3[O:41][CH2:40]2)=[O:37])=[CH:32][CH:31]=1>ClCCl>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:29][C:30]2[CH:31]=[CH:32][C:33]([CH:34]=[CH:35][C:36]([O:38][C@@H:39]3[CH:43]4[O:44][CH2:45][C@@H:46]([O:47][C:17](=[O:18])[C:16]5[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:1](=[O:4])[CH:27]=[CH2:28])=[CH:21][CH:20]=5)[CH:42]4[O:41][CH2:40]3)=[O:37])=[CH:48][CH:49]=2)=[O:18])=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18465958HCID 18465958, compoundHCID 69512330HCID 69512330, compound

Product 1

HCID 69510007HCID 69510007, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.3 g of 4-(6-acryloyloxyhexyloxy)benzoyl chloride dissolved in 40 ml of dichloromethane was added dropwise to a solution of 2.4 ml of triethylamine, 0.3 g of 4-N,N′-dimethylaminopyridine and 1.8 g of 3-(R)-hydroxy-hexahydro-furo[3,2-b]furan-6-(S)-yl 4-hydroxycinnamate (26) in 40 ml of dichloromethane. The reaction was stirred overnight at room temperature. The solution was extracted with 80 ml of 2.5 N HCl. The organic layer was washed with water, dried over MgSO4 and passed through a silica pad. The solvent was evaporated. The crude producty was recrystallised twice from ethyl acetate. 2.8 g of white crystals were obtained (yield: 61%). The melting point of the compound was 142° C.

Workup

  1. extractionThe solution was extracted with 80 ml of 2.5 N HCl
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated
  5. customThe crude producty was recrystallised twice from ethyl acetate

Sources & evidence

ORD record
ord-a48b1c9fba624640a6b0eb74c3bf8fb4
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

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