Heptane → 1-cyclopentyl N-[2-(1-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-leucinate

HRID 632565

反応式

HRID 632565 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH:35]=O)[CH2:30][CH2:29]1)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:48]1([O:53][C:54](=[O:61])[C@H:55]([CH2:57][CH:58]([CH3:60])[CH3:59])[NH2:56])[CH2:52][CH2:51][CH2:50][CH2:49]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CCCCCCC>ClC(Cl)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:29][CH2:30][CH:31]([CH2:34][CH2:35][NH:56][C@H:55]([C:54]([O:53][CH:48]2[CH2:49][CH2:50][CH2:51][CH2:52]2)=[O:61])[CH2:57][CH:58]([CH3:59])[CH3:60])[CH2:32][CH2:33]1)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8900HeptaneHCID 5049666Sodium triacetoxyborohydrideHCID 86633653L-leucine cyclopentyl ester tosylateHCID 866864202-(1-{[2,4-Bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)acetaldehyde

生成物 1

HCID 866864191-cyclopentyl N-[2-(1-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-leucinate収率 75%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

To a solution of Intermediate D (0.245 g, 0.5 mmol) in dichloroethane (10 mL) was added L-leucine cyclopentyl ester tosylate (0.398 g, 1.07 mmol) and sodium triacetoxyborohydride (0.417 g, 1.97 mmol). The mixture was stirred for one hour then loaded directly onto a silica gel column and eluted with 7:3 ethyl acetate:heptane to yield the desired product (0.250 g, 75% yield). LC/MS: m/z 667.25 [M+H]+

後処理

  1. washeluted with 7:3 ethyl acetate

出典と根拠

ORDレコード
ord-45f7d73041424261baf06287d757f1e0
出典データセット
uspto-grants-2016_04
特許番号
US09321718B2

関連ノート

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