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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0

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反応

1-Tetralone → 8-({[(Tert-butoxy)carbonyl]amino}methyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 376800

印刷プレビュー

反応式

HRID 376800 の反応式

C1(=O)[C:10]2[C:5](=[CH:6]C=CC=2)[CH2:4]CC1.C[Si](C#N)(C)C.P(Cl)(Cl)(Cl)=O.[C:23]([C:25]1[C:34]2[CH:33]=[C:32]([C:35]([O:37]C)=[O:36])[CH:31]=[CH:30][C:29]=2[CH2:28][CH2:27][CH:26]=1)#[N:24].C1([C:49]([O-:51])=[O:50])C2C(=CC=CC=2)C=CC=1>N1C=CC=CC=1.[I-].[Zn+2].[I-]>[C:49]([NH:24][CH2:23][CH:25]1[C:34]2[CH:33]=[C:32]([C:35]([OH:37])=[O:36])[CH:31]=[CH:30][C:29]=2[CH2:28][CH2:27][CH2:26]1)([O:51][C:5]([CH3:4])([CH3:6])[CH3:10])=[O:50]

参加物実験手順出典と根拠反応ノート

参加物

8

反応物 5

HCID 107241-Tetralone

HCID 24813Phosphorus oxychloride

HCID 82115Trimethylsilyl cyanide

HCID 50492651-Naphthoate

HCID 14756558Methyl 8-cyano-5,6-dihydro-2-naphthoate

生成物 1

HCID 193591728-({[(Tert-butoxy)carbonyl]amino}methyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

試薬・触媒・溶媒

2

HCID 9883512zinc(II)iodide触媒

HCID 1049Pyridine溶媒

実験手順

As shown above in Scheme 7, the remaining tetralone was then converted to the methyl ester (9). Using a procedure from Gregory, G. B. and Johnson, A. L, JOC, 1990, 55, 1479, the tetralone methyl ester (9) was converted, first, to the cyanohydrin by treatment with trimethylsilylcyanide and zinc iodide and then, via the in situ dehydration with phosphorous oxychloride in pyridine, to the methyl 8-cyano-5,6-dihydro-2-naphthoate (11). This naphthoate was divided into two portions and some was subjected to hydrogenolysis, N-BOC-protection and saponification to give N-(BOC)-8-aminomethyl-5,6,7,8-tetrahydro-2-naphthoic acid (12) as an intermediate for incorporation into the cyclic peptide.

出典と根拠

ORDレコード: ord-eae8810a21b24f76b25cbbbfd355810d
出典データセット: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06022523

反応ノート

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