Hydrochloric Acid → N(alpha)-(N(alpha)-(N(alpha)-(tert-butyloxycarbonyl)glutaminyl)-N(1)-formyl-tryptophyl)phenylalanine benzyl ester

HRID 2082222ノート

反応式

HRID 2082222 の反応式
[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:2]([C:8]([OH:10])=O)[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].Cl.[NH2:19][C@@H:20]([C:33]([NH:35][C@H:36]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:34])[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]([CH:31]=[O:32])[CH:23]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(Cl)Cl>[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:2]([C:8]([NH:19][C@@H:20]([C:33]([NH:35][C@H:36]([C:44]([O:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:45])[CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:34])[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]([CH:31]=[O:32])[CH:23]=1)=[O:10])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 83687L-Glutamine, N2-((1,1-dimethylethoxy)carbonyl)-HCID 15755292HCID 15755292、化合物

生成物 1

HCID 130847N(alpha)-(N(alpha)-(N(alpha)-(tert-butyloxycarbonyl)glutaminyl)-N(1)-formyl-tryptophyl)phenylalanine benzyl ester収率 95.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of Boc-Gln-OH (2.10 g), HCl.H-D-Trp(CHO)-Phe-OBzl (4.70 g) and HOBT (1.15 g) in a mixed solvent of methylene chloride (60 ml) and DMF (10 ml), was added WSC (1.41 g) under ice cooling. The reaction mixture was stirred for 1.5 hours at the same temperature and for additional 1.5 hours at room temperature and concentrated under reduced pressure. Water was added to the residue and the resulting precipitates were collected and washed successively with water, diluted sodium hydrogencarbonate solution and water. After drying, the crude product (5.84 g) was stirred in hot ethyl acetate (60 ml) in water bath. After cooling, the precipitates were collected by filtration and dried to give Boc-Gln-D-Trp(CHO)-Phe-OBzl (5.70 g).

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the residue
  3. customthe resulting precipitates
  4. customwere collected
  5. washwashed successively with water, diluted sodium hydrogencarbonate solution and water
  6. customAfter drying
  7. stirringthe crude product (5.84 g) was stirred in hot ethyl acetate (60 ml) in water bath
  8. temperatureAfter cooling
  9. filtrationthe precipitates were collected by filtration
  10. customdried

出典と根拠

ORDレコード
ord-5f39904082c44f63a04a9d201caf1a24
出典データセット
uspto-grants-1993_02
特許番号
US05187156

反応ノート

読み込み中…