Ammonium Chloride → HCID 86597944、化合物

HRID 854653ノート

反応式

HRID 854653 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH:22]=O)[CH2:17]1.[NH2:24][C@H:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:26]([CH3:28])[CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[Cl-]>ClCCl.O.CC(O)=O>[CH3:27][CH:26]([CH3:28])[C@H:25]([NH:24][CH2:22][C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:16]([O:15][CH2:14][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])[CH2:17]1)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 114626tert-Butyl L-valinateHCID 5049666Sodium triacetoxyborohydrideHCID 86597945cis-3-(5-Methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexanecarbaldehyde

生成物 1

HCID 86597944HCID 86597944、化合物収率 99%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

511 mg of cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexanecarbaldehyde, 0.9 ml of HOAc and 310 mg of tert-butyl (S)-valinate are dissolved in 5 ml of abs. dichloromethane. 500 mg of molecular sieve 4 Å are then added, and the suspension is cooled to 0° C. 414 mg of sodium triacetoxyborohydride are added a little at a time. This suspension is stirred at 0° C. for 2 h, 3 ml of saturated NH4Cl solution are then added and the suspension is stirred for a further 10 min. In each case 10 ml of water and dichloromethane are added, the phases are separated, the aqueous phase is extracted with dichloromethane and the combined organic phases are dried over MgSO4 and concentrated, which gives 760 mg of tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]-amino}butyrate. C28H42N2O4 (470.66); MS (ESI): 471.50 (MH+).

後処理

  1. addition500 mg of molecular sieve 4 Å are then added
  2. stirringthe suspension is stirred for a further 10 min
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. dry with materialthe combined organic phases are dried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-09f64f4ba2fe44ccb7115b1bf25fc90f
出典データセット
uspto-grants-2007_08
特許番号
US07259177B2

反応ノート

読み込み中…