Triethylamine → (S)-4-(Benzyloxycarbonyl)-1-(diphenylacetyl)piperazine-2-carboxylic acid

HRID 486747ノート

反応式

HRID 486747 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C@H:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27]1([CH:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:34](=[O:35])[CH:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 746372,2-Diphenylacetyl chlorideHCID 1514273(S)-4-(Benzyloxycarbonyl)piperazine-2-carboxylic acid

生成物 1

HCID 22850671(S)-4-(Benzyloxycarbonyl)-1-(diphenylacetyl)piperazine-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A solution of 1.00 g (3.78 mmole) of (S)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid (from Example 7, Step A) in 10 ml of DMF at 25° C. was treated with 0.755 g. (7.46 mmole) of triethylamine. The solution was cooled to 0° C. and 0.95 g (4.12 mmole) of diphenylacetyl chloride was added in Portions over 2 hours. The solution was stirred at 25° C. for 64 hours, concentrated in vacuo and partitioned between 60 ml. of 1N HCl and 60 ml of ethyl acetate. The ethyl acetate was dried over sodium sulfate, concentrated in vacuo and chromatographed in two portions over an 85×2.5 cm LH-20 column with 11 ml fractions of methanol. Fractions 38-41 from both columns were combined and concentrated in vacuo to 785 mg (44%) of oil which was homogeneous by TLC (80:20:2 chloroform-methanol-ammonia water, Rf =0.40).

後処理

  1. concentrationconcentrated in vacuo
  2. custompartitioned between 60 ml
  3. dry with materialThe ethyl acetate was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customchromatographed in two portions over an 85×2.5 cm
  6. concentrationconcentrated in vacuo to 785 mg (44%) of oil which

出典と根拠

ORDレコード
ord-676822223e0e4b51828763b5804e2edf
出典データセット
uspto-grants-1994_03
特許番号
US05292726

反応ノート

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