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

HRID 486747노트

반응식

HRID 486747 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-676822223e0e4b51828763b5804e2edf
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292726

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