Diisopropylethylamine → Morpholine-4-carboxylic acid[(r)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide

HRID 460410ノート

反応式

HRID 460410 の反応式
[NH2:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][CH2:4][CH:3]1[OH:9].C(N(C(C)C)CC)(C)C.[N:19]1([C:25]([NH:27][C@@H:28]([CH2:32][S:33]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:35])=[O:34])[C:29](O)=[O:30])=[O:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[OH:9][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[CH:2]1[NH:1][C:29]([C@@H:28]([NH:27][C:25]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:26])[CH2:32][S:33]([CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)(=[O:35])=[O:34])=[O:30]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 3196702-Aminocyclohexane-1,3-diolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11439693(R)-2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid

生成物 1

HCID 86612924Morpholine-4-carboxylic acid[(r)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide収率 10.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-amino-cyclohexane-1,3-diol (0.55 g) in dimethylformamide (30 ml) was treated with diisopropylethylamine (1.6 ml, 9.2 mmol). After stirring at room temperature for 5 minutes the mixture was treated with (R)-2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid (1.73 g, 4.86 mmol) followed by HATU (1.68 g, 4.42 mmol). This mixture was stirred at room temperature overnight and then evaporated. The residue was subjected to flash chromatography on silica eluting with ethyl acetate and then a mixture of ethyl acetate and methanol to give morpholine-4-carboxylic acid [(R)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide as a white solid (210 mg). MS: 470 (MH+).

後処理

  1. stirringThis mixture was stirred at room temperature overnight
  2. customevaporated
  3. additiona mixture of ethyl acetate and methanol

出典と根拠

ORDレコード
ord-82b8d578b0014890a5bb0029e1078d47
出典データセット
uspto-grants-2007_03
特許番号
US07196099B2

反応ノート

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