HCID 57786475、化合物 → HCID 57786470、化合物

HRID 253597

反応式

HRID 253597 の反応式
[Cl:1][C:2]1[C:3]([F:46])=[C:4]([C@:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([NH:24][C@@H:25]([CH2:39][CH:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)[C@@H:26]([OH:38])[CH2:27][NH:28]C(=O)OCC[Si](C)(C)C)=[O:23])[CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1>C(#N)C.[F-].C([N+](CC)(CC)CC)C>[NH2:28][CH2:27][C@H:26]([OH:38])[C@@H:25]([NH:24][C:22]([N:18]1[CH2:19][CH2:20][CH2:21][C@@H:16]([C@@:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:46])([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH2:17]1)=[O:23])[CH2:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

参加物

4

反応物 1

HCID 57786475HCID 57786475、化合物

生成物 1

HCID 57786470HCID 57786470、化合物収率 117%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2-(trimethylsilyl)ethyl (2S,3S)-3-((R)-3-((S)-1-(3-chloro-2-fluorophenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-4-cyclohexyl-2-hydroxybutylcarbamate (25.8 mg, 0.038 mmol) in acetonitrile (2 mL), tetraethylammonium fluoride (excess) was added. The resulting solution was stirred at 50° C. for 2 h, and purified directly with preparative HPLC to give (R)-N-((2S,3S)-4-amino-1-cyclohexyl-3-hydroxybutan-2-yl)-3-((S)-1-(3-chloro-2-fluorophenyl)-1-hydroxy-5-methoxy-pentyl)piperidine-1-carboxamide (24.1 mg, 96%) as its TFA salt; 1H NMR (400 MHz, CD3OD) δ 7.54 (dd, 1H), 7.38 (dd, 1H), 7.14 (dd, 1H), 4.36 (d, 1H); 3.94 (m, 2H), 3.78 (m, 1H), 3.28 (m, 2H), 3.24 (s, 3H), 2.94 (dd, 1H), 2.84 (m, 2H), 2.64 (dd, 1H), 2.16 (m, 1H), 1.98 (m, 3H), 0.78-1.86 (m, 20H); MS m/z 542 (M+H+).

後処理

  1. custompurified directly with preparative HPLC

出典と根拠

ORDレコード
ord-9154da3018cb4d97b57ac951db782f44
出典データセット
uspto-grants-2011_01
特許番号
US07872028B2

関連ノート

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