Triethylamine → HCID 69585605、化合物

HRID 1242117ノート

反応式

HRID 1242117 の反応式
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][C@@H:14]([C:17](O)=[O:18])[N:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.Cl.[NH2:44][C@H:45]([C:49]([OH:51])=O)[CH2:46][CH2:47][SH:48]>O1CCCC1>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][C@@H:14]([C:17](=[O:18])[NH:44][CH:45]3[CH2:46][CH2:47][S:48][C:49]3=[O:51])[N:13]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:27])=[O:7])([CH3:2])([CH3:4])[CH3:3]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 69585611HCID 69585611、化合物HCID 71587034Homocysteine hydrochloride

生成物 1

HCID 69585605HCID 69585605、化合物収率 56.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,5-(S),6-tri-carboxylic acid 3,6-di-tert-butyl ester (0.30 g, 0.75 mmol) and triethylamine (0.21 mL, 1.51 mmol) in tetrahydrofuran (10 mL) was cooled to −20° C. before isobutyl chloroformate (0.103 mL, 0.75 mmol) was added. The reaction mixture was stirred 15 min at −20° C. before homocystein hydrochloride (116 mg, 0.75 mmol) was added. The cooling bath was removed and the reaction mixture was left for 16 hours at room temperature. The solvent was removed in vacuo and the residue was subjected to column chromatography (SiO2, Flash 40, heptane/ethyl acetate 2:1) to give 212 mg (56%) of 2-amino-5-(S)-(2-oxo-tetrahydro-thiophen-3-ylcarbamoyl)-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester

後処理

  1. additionwas added
  2. additionwas added
  3. customThe cooling bath was removed
  4. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-0ef6fb33719344f981b28aa8e62527f2
出典データセット
uspto-grants-2006_10
特許番号
US07115624B1

反応ノート

読み込み中…