Benzyl Alcohol → HCID 131713397、化合物

HRID 1388693ノート

反応式

HRID 1388693 の反応式
[C:1]1([P:7](Cl)(Cl)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.Cl.[NH2:27][C@H:28]([C:36]([NH:38][C@H:39]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[C:12]1([CH2:11][O:18][P:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([NH:27][C@H:28]([C:36]([NH:38][C@H:39]([C:44]([O:46][CH2:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:45])[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:37])[CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:8])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 8471Triethylamine2 回HCID 69990Phenylphosphonic dichlorideHCID 70633701HCID 70633701、化合物

生成物 1

HCID 131713397HCID 131713397、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A mixture of phenylphosphonic dichloride (1.15 ml., 8 mmole) and dry dichloromethane (15 ml.) under argon at 25° is treated dropwise with benzyl alcohol (0.83 ml., 1 eq.) and triethylamine (1.1 ml., 1 eq.) in dichloromethane (5 ml.) over a 20 minute period. A slight exotherm is observed. The reaction mixture is then refluxed for 15 minutes, cooled to 0° (ice bath), and L-phenylalanyl-L-leucine, phenylmethyl ester, hydrochloride salt (1 eq.) is added. The heterogeneous mixture is treated dropwise with triethylamine (2.4 ml., 2.1 eq.) in dichloromethane (8 ml.) over a 5 minute period. The ice bath is removed and the reaction mixture is stirred for an additional 1.5 hours. The solids are removed by filtration and the dichloromethane is stripped from the filtrate. The residue is taken up in ethyl acetate and washed with water, saturated sodium bicarbonate, 5% potassium bisulfate, saturated sodium bicarbonate, brine, dried (MgSO4), and evaporated to a residue. The residue is purified chromatographically to give N-[N-[phenylmethoxy(phenyl)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester.

後処理

  1. temperatureThe reaction mixture is then refluxed for 15 minutes
  2. additionis added
  3. customThe ice bath is removed
  4. customThe solids are removed by filtration
  5. washwashed with water, saturated sodium bicarbonate, 5% potassium bisulfate, saturated sodium bicarbonate, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to a residue
  8. customThe residue is purified chromatographically

出典と根拠

ORDレコード
ord-376a4de861cc462aa607956cda695741
出典データセット
uspto-grants-1984_02
特許番号
US04432972

反応ノート

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