Lithium Hydroxide → Tert-butyl (s)-1-((s)-1-((2s,4s)-4-azido-2-((r)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate

反応式

[N:1]([C@@H:4]1[CH2:8][N:7]([C:9](=[O:29])[C@@H:10]([NH:15][C:16](=[O:28])[C@@H:17]([N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH3:20])[CH3:18])[C:11]([CH3:14])([CH3:13])[CH3:12])[C@H:6]([C:30]([O:32]C)=O)[CH2:5]1)=[N+:2]=[N-:3].[Li+].[OH-].[C@H:36]1([NH2:46])[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][CH2:37]1>>[N:1]([C@@H:4]1[CH2:8][N:7]([C:9](=[O:29])[C@@H:10]([NH:15][C:16](=[O:28])[C@@H:17]([N:19]([CH3:20])[C:21](=[O:22])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:18])[C:11]([CH3:14])([CH3:13])[CH3:12])[C@H:6]([C:30](=[O:32])[NH:46][C@H:36]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:39][CH2:38][CH2:37]2)[CH2:5]1)=[N+:2]=[N-:3]

参加物

反応物 3

HCID 3939Lithium Hydroxide

HCID 70580721-Aminotetralin, (R)-

HCID 57661019(2s,4s)-Methyl 4-azido-1-((s)-2-((s)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylate

生成物 1

HCID 57661012Tert-butyl (s)-1-((s)-1-((2s,4s)-4-azido-2-((r)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate

実験手順

The title compound of Example 2 was treated with LiOH using the general procedure C to hydrolyze the methyl ester. The resulting acid was coupled to (R)-tetrahydro-1-naphthylamine using the general procedure D to prepare the title compound of Example 3. 1H NMR (CDCl3): consistent with proposed structure.

出典と根拠

ORDレコード: ord-9a9965aafb904556af148d73b96fbf6d
出典データセット: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08642554B2

反応ノート

読み込み中…