Dicyclohexylcarbodiimide → Z-Sta-Ile-His-Lys(Boc)-OMe

HRID 1982310노트

반응식

HRID 1982310 반응식
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C@H:7]([CH2:9][C:10]([OH:12])=O)[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:23][C@H:24]([C:29]([NH:31][C@H:32]([C:39]([NH:41][C@H:42]([C:55]([O:57][CH3:58])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[O:40])[CH2:33][C:34]1[N:38]=[CH:37][NH:36][CH:35]=1)=[O:30])[C@H:25]([CH2:27][CH3:28])[CH3:26].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.O>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C@H:7]([CH2:9][C:10]([NH:23][C@H:24]([C:29]([NH:31][C@H:32]([C:39]([NH:41][C@H:42]([C:55]([O:57][CH3:58])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])=[O:40])[CH2:33][C:34]1[N:38]=[CH:37][NH:36][CH:35]=1)=[O:30])[C@H:25]([CH2:27][CH3:28])[CH3:26])=[O:12])[OH:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14560231Z-Sta-OHHCID 178455961HCID 178455961, 화합물

생성물 1

HCID 178455902Z-Sta-Ile-His-Lys(Boc)-OMe

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

900 mg of Z-Sta-OH (for manufacture see stage 1.12), 1.24 g of H-Ile-His-Lys(Boc)-OMe and 560 mg of HOBt×H2O are dissolved in 13 ml of DMF. After the addition of 600 mg of DCCI, the whole is left to stand at room temperature for 20 hours, then the DCH which has crystallised out is filtered off and the filtrate is concentrated to dryness. The greasy residue is triturated at 0° with 30 ml of diisopropyl ether, the solvent is decanted and the residue is dried. Purification is carried out by Craig partitioning in the system methanol/buffer/ethylene chloride/chloroform (10:3:8:4; buffer=14.3 ml of glacial acetic acid and 9.6 g of ammonium acetate in 1000 ml of H2O) over 700 stages. The thin layer chromatographically pure fractions (K=0.5) are combined, strongly concentrated and lyophilised. To remove acetic acid, the product is dissolved and reprecipitated from 5% strength methanolic NaHCO3 solution, yielding Z-Sta-Ile-His-Lys(Boc)-OMe in the form of amorphous powder; Rf (B)=0.8; Rf (I)=0.56.

후처리

  1. waitthe whole is left
  2. customthe DCH which has crystallised out
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated to dryness
  5. customThe greasy residue is triturated at 0° with 30 ml of diisopropyl ether
  6. customthe solvent is decanted
  7. customthe residue is dried
  8. customPurification
  9. custompartitioning in the system methanol/buffer/ethylene chloride/chloroform (10:3:8:4; buffer=14.3 ml of glacial acetic acid and 9.6 g of ammonium acetate in 1000 ml of H2O) over 700 stages
  10. concentrationstrongly concentrated
  11. customTo remove acetic acid
  12. dissolutionthe product is dissolved
  13. customreprecipitated from 5% strength methanolic NaHCO3 solution

출처 및 근거

ORD 기록
ord-e32981ec52c04655b8b1c9f76a43e0db
출처 데이터셋
uspto-grants-1986_06
특허 번호
US04595677

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