Dicyclohexylcarbodiimide → Z-Trp-Pro-OBut

HRID 1154157

반응식

HRID 1154157 반응식
C1CCC(N=C=NC2CCCCC2)CC1.[NH:16]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:17]([C:28]([OH:30])=O)[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1.[NH:41]1[CH2:52][CH2:51][CH2:50][C@H:42]1[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:16]([C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[C@H:17]([C:28]([N:41]1[CH2:52][CH2:51][CH2:50][C@H:42]1[C:43]([O:45][C:46]([CH3:48])([CH3:49])[CH3:47])=[O:44])=[O:30])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 101176benzyloxycarbonyl-L-tryptophanHCID 6453108L-Proline 1,1-dimethylethyl ester

생성물 1

HCID 13178803Z-Trp-Pro-OBut

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

10.92 g (53 mmoles) of DCC are added at 0° C. to a solution of 16.9 g (50 mmoles) of Z-Trp-OH, 8.55 g (50 mmoles) of H-Pro-OBut and 6.75 g (50 mmoles) of HOBt in 75 ml of dimethylformamide. The mixture is stirred for 2 hours at 0° C. and left to stand overnight at room temperature. The precipitate is filtered off and the filtrate is concentrated. The residue is worked up analogously to Example 1 a. The residue is triturated with ether. Yield 19.49 g (79%), melting point 173°, [α]D25 =-54.2° (c=1, dimethylformamide).

후처리

  1. waitleft
  2. waitto stand overnight at room temperature
  3. filtrationThe precipitate is filtered off
  4. concentrationthe filtrate is concentrated
  5. customThe residue is triturated with ether
  6. customYield 19.49 g (79%), melting point 173°, [α]D25 =-54.2° (c=1, dimethylformamide)

출처 및 근거

ORD 기록
ord-d31d4dc102284d9abf1553600d7eff4d
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04487764

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