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(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate → 2-[2-Chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propylcarbamoyl]-5-propyl-azepane-1-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester

HRID 901470
ノート
印刷プレビュー

反応式

HRID 901470 の反応式
[Cl:1][CH:2]([CH3:28])[CH:3]([NH:15][C:16]([CH:18]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20][NH:19]1)=[O:17])[CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1.[N+](C1C=CC([O:38][C:39](=O)[O:40][CH2:41][C:42]2[O:43][C:44](=[O:48])[O:45][C:46]=2[CH3:47])=CC=1)([O-])=O>CN(C=O)C>[CH3:47][C:46]1[O:45][C:44](=[O:48])[O:43][C:42]=1[CH2:41][O:40][C:39]([N:19]1[CH2:20][CH2:21][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:24][CH:18]1[C:16](=[O:17])[NH:15][CH:3]([CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1)[CH:2]([Cl:1])[CH3:28])=[O:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 10756264(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonateHCID 730964105-Propyl-azepane-2-carboxylic acid [2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

生成物 1

HCID 692210762-[2-Chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propylcarbamoyl]-5-propyl-azepane-1-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester収率 33.6%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

The title compound from example 47 (54 mg, 0.12 mmol) was dissolved in dry DMF (5 mL), then solid KHCO3 (25 mg, 0.25 mmol) and carbonic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester 4-nitro-phenyl ester (40 mg, 0.14 mmol prepared as described in F. Sakamoto, et. al, Chem. Pharm. Bull. 1984, 32 (6), 2241-2348) were added. The resulting mixture was stirred for 16 h, and the solvents were removed under reduced pressure, then the residue was purified by chromatography on silica with 5% MeOH/DCM to provide the title compound (24 mg, 33%) as a white solid.

後処理

  1. customthe solvents were removed under reduced pressure
  2. customthe residue was purified by chromatography on silica with 5% MeOH/DCM

出典と根拠

ORDレコード
ord-8e5d262ea6a94787a9c715c5512b5d39
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07361743B2

反応ノート

読み込み中…

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