D-Tryptophan → HCID 45254561, compound

HRID 2065620Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[C:11]([Cl:17])[CH:10]=2)=[O:5])C.[NH2:19][C@@H:20]([C:31]([OH:33])=[O:32])[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1>>[C:31]([C@H:20]([NH:19][C:7]1[C:6]([C:4]([OH:3])=[O:5])=[CH:15][C:14]2[C:9](=[CH:10][C:11]([Cl:17])=[C:12]([Cl:16])[CH:13]=2)[N:8]=1)[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)([OH:33])=[O:32]

Participants

Reactant 2

HCID 9060D-Tryptophan

HCID 86656376HCID 86656376, compound

Product 1

HCID 45254561HCID 45254561, compoundYield 29%

Procedure

In close analogy to the procedure described in Example 32, 2,6,7-trichloroquinoline-3-carboxylic acid ethyl ester is reacted with D-tryptophan (heating for 39 h) to provide the title compound in 29% yield as pale yellow powder.

Sources & evidence

ORD record: ord-61af8adce192470f8a51f518066b35d9
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288549B2

Reaction notes

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