Hydrochloric Acid → HCID 70248038, compound

HRID 1533281Notes

Reaction equation

HRID 1533281 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[OH:15])[C:11](O)=[O:12])=[CH:4][C:3]=2[O:2]1.Cl.[NH2:23][C@H:24]([C:35]([O:37][CH3:38])=[O:36])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[CH3:38][O:37][C:35](=[O:36])[C@H:24]([CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)[NH:23][C:11](=[O:12])[CH:10]([C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)[CH:14]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[OH:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 77980L-Tryptophan, methyl esterHCID 22012326HCID 22012326, compound

Product 1

HCID 70248038HCID 70248038, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-cyclohexyl-3-hydroxypropionic acid (100 mg), HCl.H-L-Trp-OMe (136 mg) and HOBT (55 mg) in dimethylformamide (6 ml) was added WSCD (64 mg) under ice-bath cooling. After being stirred overnight at room temperature, the mixture was poured into water (20 ml) and extracted with ethyl acetate (20 ml). The organic layer was washed with 5% hydrochloric acid solution, 1M aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo to afford N-[(2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-cyclohexyl-3-hydroxypropionyl]-L-tryptophane methyl ester (165 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (20 ml)
  3. washThe organic layer was washed with 5% hydrochloric acid solution, 1M aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40b40a20af734f1ba5282aeb3667b53e
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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