1-Methylimidazole → (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-4-pyrimidinyl-3-pyrazolidinecarboxamide

HRID 1396886ノート

反応式

HRID 1396886 の反応式
CN1C=CN=C1.[CH:7]1([CH2:12][C@H:13]([CH2:34][N:35]([CH:44]=[O:45])[O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:14]([N:16]2[C@H:20]([C:21]([OH:23])=O)[CH2:19][CH2:18][N:17]2[C:24](OCC2C=CC=CC=2)=O)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]1.S(Cl)(C)(=O)=O.[NH2:51][C:52]1[CH:57]=[CH:56][N:55]=[CH:54][N:53]=1>CN(C=O)C>[CH:7]1([CH2:12][C@H:13]([CH2:34][N:35]([CH:44]=[O:45])[O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:14]([N:16]2[C@H:20]([C:21]([NH:51][C:52]3[CH:57]=[CH:56][N:55]=[CH:54][N:53]=3)=[O:23])[CH2:19][CH2:18][N:17]2[CH3:24])=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]1

参加物

6

反応物 4

HCID 13901-MethylimidazoleHCID 31297Methanesulfonyl chlorideHCID 689584-AminopyrimidineHCID 86706346(3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid

生成物 1

HCID 86706352(3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-4-pyrimidinyl-3-pyrazolidinecarboxamide収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

1-Methylimidazole (38.2 μl, 0.479 mmol) was added into a solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidine carboxylic acid (100 mg, 0.240 mmol) in 1.0 ml of DMF. The solution was cooled to 0° C., and then mesyl chloride (24.26 μl, 0.311 mmol) was added dropwise at 0° C. 4-Aminopyrimidine (34.2 mg, 0.359 mmol) dissolved in another 1.0 ml of DMF was then added. The reaction mixture was stirred for 3.5 h at rt. The reaction mixture was concentrated and purified by RP-HPLC to afford (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-4-pyrimidinyl-3-pyrazolidinecarboxamide (95 mg, 0.192 mmol, 80%) as a white foam solid. LC-MS (ES) m/e 495.3 (M+H)+.

後処理

  1. additionwas then added
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by RP-HPLC

出典と根拠

ORDレコード
ord-38f72d16c4114e298c84b5f8b0b8693d
出典データセット
uspto-grants-2014_12
特許番号
US08901119B2

反応ノート

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