Allyl Alcohol → HCID 11426846, compound

HRID 1823643Notes

Reaction equation

HRID 1823643 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@@:8]1([C:17]([OH:19])=[O:18])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[C@H:10]2[C:14]([OH:16])=[O:15])=[O:6])[CH:2]=[CH2:3].C(N=C=N[CH2:25][CH2:26][CH2:27]N(C)C)C.CN(C1C=CC=CN=1)C.C(O)C=C>C(Cl)Cl>[CH2:27]([O:15][C:14]([C@@H:10]1[C@@H:9]2[C@H:11]1[CH2:12][CH2:13][C@@:8]2([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[C:17]([OH:19])=[O:18])=[O:16])[CH:26]=[CH2:25]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 11196464HCID 11196464, compound

Product 1

HCID 11426846HCID 11426846, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(1S,2S,5R,6S)-2-Allyloxycarbonylamino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (13.4 g, 49.81 mmol, 1.0 equiv) was suspended in methylene chloride (400 mL). N-Ethyl-N′-dimethylaminopropylcarbodiimide (9.55 g, 49.81 mmol, 1.0 equiv) and dimethylaminopyridine (0.608 g, 4.98 mmol, 0.1 equiv) were added at room temperature under nitrogen. After a solution formed, allyl alcohol (3.4 mL, 2.89 g, 49.81 mmol, 1.0 equiv) was added and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with methylene chloride and washed twice with water. The organic phase was dried over magnesium sulfate, filtered and concentrated. The title compound was obtained as an oil (44% yield).

Workup

  1. customAfter a solution formed
  2. washwashed twice with water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-018d42a32d5b4eefb332170afb56ccb9
Source dataset
uspto-grants-2006_05
Patent number
US07038077B2

Reaction notes

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