O-Methyl-L-Tyrosine → (S)-N-[2-Azido-1-(4-methoxybenzyl)ethyl]-4-hydroxy-1-methyl-1H-indole-2-carboxamide

HRID 749316Notes

Reaction equation

HRID 749316 reaction equation
[N:1]([CH2:4][C@@H:5]([NH2:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[N+:2]=[N-:3].N[C@@H](CC1C=CC(OC)=CC=1)C[OH:19].COC1C=CC(C[C@@H](C(O)=O)N)=CC=1.O[C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[N:46]([CH3:53])[C:45]=1[C:54]([OH:56])=O>>[N:1]([CH2:4][C@@H:5]([NH:15][C:54]([C:45]1[N:46]([CH3:53])[C:47]2[C:52]([CH:44]=1)=[C:51]([OH:19])[CH:50]=[CH:49][CH:48]=2)=[O:56])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 4

HCID 2723935O-Methyl-L-TyrosineHCID 11788635(betaS)-beta-Amino-4-methoxybenzenepropanolHCID 547114253-Hydroxy-1-methyl-1H-indole-2-carboxylic acidHCID 86601457(S)-1-azido-3-(4-methoxyphenyl)-2-propanamine

Product 1

HCID 86601456(S)-N-[2-Azido-1-(4-methoxybenzyl)ethyl]-4-hydroxy-1-methyl-1H-indole-2-carboxamide

Procedure

From (S)-1-azido-3-(4-methoxyphenyl)-2-propanamine [prepared by an adaptation of a method described by Horwell, et al., J. Med. Chem., 1991, 404-414 from (S)-2-amino-3-(4-methoxyphenyl)-1-propanol (prepared from O-methyl-L-tyrosine by an adaptation of a method described by Sutherland, et al., J Org Chem, 1998, 7764-7769] and 4 hydroxy-1-methyl-1H-indole-2-carboxylic acid the title compound was prepared by a method analogous to that described in Example 13. MS ES (M++H)=380.

Sources & evidence

ORD record
ord-49ea01ca50984b68bf04d43c36f2840a
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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