Acetic Anhydride → 2,3-Dihydromelatonin

HRID 370063Notes

Reaction equation

HRID 370063 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH:6]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH2:5]1)(=O)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH2:27][CH:26]2[CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36].Cl[C:39]([O:41][CH2:42][CH3:43])=[O:40].C(OC(=O)C)(=O)C.FC(F)(F)S(N1C2[C:59](=[CH:60]C(OC)=CC=2)[CH:58]([CH2:67][CH2:68]N(C(C)=O)C(=O)C)C1)(=O)=O>ClCCl.C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:14][O:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH2:5][CH:6]2[CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19].[CH2:42]([O:41][C:39]([N:28]1[C:29]2[C:25](=[CH:24][C:23]([O:22][CH3:21])=[CH:31][CH:30]=2)[CH:26]([CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36])[CH2:27]1)=[O:40])[C:43]1[CH:68]=[CH:67][CH:58]=[CH:59][CH:60]=1

Participants

10

Reactant 5

HCID 7918Acetic AnhydrideHCID 10928Ethyl chloroformateHCID 101308722,3-DihydromelatoninHCID 23283701N-[2-(1-acetyl-5-methoxyindolin-3-yl)ethyl]acetamideHCID 69944386N-[2-(1-trifluoromethanesulphonyl-5-methoxyindolin-3-yl)ethyl]diacetamide

Product 2

HCID 101308722,3-DihydromelatoninHCID 23283708N-[2-(1-benzyloxycarbonyl-5-methoxyindolin-3-yl)ethyl]acetamide

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

N-[2-(5-Methoxyindolin-3-yl)ethyl]acetamide is prepared by the method described for the synthesis of N-[2-(1-acetyl-5-methoxyindolin-3-yl)ethyl]acetamide. The intermediate N-[2-(1-benzyloxycarbonyl-5-methoxyindolin-3-yl)ethyl]acetamide is prepared by reacting the N-[2-(5-methoxyindolin-3-yl)ethyl]acetamide with ethyl chloroformate in dichloromethane at 0° C. in the presence of triethylamine. The final acylation is carried out with acetic anhydride in refluxing toluene for 24 h, and allows N-[2-(1-trifluoromethanesulphonyl-5-methoxyindolin-3-yl)ethyl]diacetamide to be obtained.

Workup

  1. customat 0° C.
  2. customto be obtained

Sources & evidence

ORD record
ord-d63bc78a383340c0b0b0c2625c9fd602
Source dataset
uspto-grants-2000_10
Patent number
US06140372

Reaction notes

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