Propargyl alcohol → HCID 20205910, compound

HRID 543237Notes

Reaction equation

HRID 543237 reaction equation
[C:1]([NH:9][CH:10]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](O)[C:25]#[CH:26].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([NH:9][CH:10]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[C:11]([O:13][CH2:26][C:25]#[CH:24])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 10868DicyclohexylcarbodiimideHCID 2948912-benzamido-3-(1H-indol-3-yl)propanoic acid

Product 1

HCID 20205910HCID 20205910, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(benzoylamino)-3-(indol-3-yl)propanoic acid (1.9 g) was dissolved in 75 ml of dry methylene chloride (from phosphorous pentoxide). The solution was cooled to 0° C. in an ice bath and 0.72 ml of propargyl alcohol was added along with 1.39 g of DCC followed by 0.07 g DMAP. The reaction mixture was warmed to room temperature and maintained there for 16 hours. The solution was filtered into a separatory funnel, washed with 5% acetic acid (2×), water (1×) and 5% solution bicarbonate (1×). The separated methylene chloride layer was then dried over magnesium sulfate and evaporated to dryness. The residue was redissolved in ethyl acetate, filtered and the filtrate evaporated to dryness. The orangish residue was dried in vacuo to give propargyl 2-(benzoylamino)-3-(indol-3-yl)propionate.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. temperaturemaintained there for 16 hours
  3. filtrationThe solution was filtered into a separatory funnel
  4. washwashed with 5% acetic acid (2×), water (1×) and 5% solution bicarbonate (1×)
  5. dry with materialThe separated methylene chloride layer was then dried over magnesium sulfate
  6. customevaporated to dryness
  7. dissolutionThe residue was redissolved in ethyl acetate
  8. filtrationfiltered
  9. customthe filtrate evaporated to dryness
  10. customThe orangish residue was dried in vacuo

Sources & evidence

ORD record
ord-1d38b6c30064478e9f634029882ea6d5
Source dataset
uspto-grants-1987_04
Patent number
US04661510

Reaction notes

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