Pyridine → HCID 20640759, compound

HRID 1533287Notes

Reaction equation

HRID 1533287 reaction equation
[CH2:1]([O:8][C:9](=[O:40])[C@H:10]([CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)[NH:11][C:12](=[O:29])[CH:13]([C:20]1[CH:25]=[CH:24][C:23]2[O:26][CH2:27][O:28][C:22]=2[CH:21]=1)[CH:14]([OH:19])[CH2:15][CH2:16][CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:47](OC(=O)C)(=[O:49])[CH3:48]>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9](=[O:40])[C@H:10]([CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)[NH:11][C:12](=[O:29])[CH:13]([C:20]1[CH:25]=[CH:24][C:23]2[O:26][CH2:27][O:28][C:22]=2[CH:21]=1)[CH:14]([O:19][C:47](=[O:49])[CH3:48])[CH2:15][CH2:16][CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 20640766HCID 20640766, compound

Product 1

HCID 20640759HCID 20640759, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Nα-[(2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-hydroxyheptanoyl]-L-tryptophan benzyl ester (255 mg) in dichloromethane (5 ml) were added pyridine (74 mg), acetic anhydride (72 mg) and 4-(dimethylamino)pyridine (11 mg) at 5° C. and the mixture was stirred at ambient temperature for 18 hours. The mixture was diluted with ethyl acetate (20 ml) and the solution was washed with 0.5N hydrochloric acid (20 ml×2), saturated sodium bicarbonate aqueous solution (20 ml×2) and brine (20 ml) successively and the organic layer was dried over magnesium sulfate. The solution was filtered and concentrated in vacuo to give Nα-[(2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-acetoxyheptanoyl]-L-tryptophan benzyl ester as an oil.

Workup

  1. washthe solution was washed with 0.5N hydrochloric acid (20 ml×2), saturated sodium bicarbonate aqueous solution (20 ml×2) and brine (20 ml) successively
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationThe solution was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-789455f7dd8541a5a8c21502fb100ce6
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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