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Hydrochloric Acid → HCID 178427569、化合物

HRID 743146
ノート
印刷プレビュー

反応式

HRID 743146 の反応式
[N:1]1([C:13]([O:15]C(C)(C)C)=O)[CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([NH:5][CH2:6][C:7]([NH2:9])=[O:8])=[O:4].Cl.C(OCC)C.Cl.C[O-].[Na+].C1C=CC2N(O)N=NC=2C=1.[NH:40]([C:70]([O:72][CH2:73][CH:74]1[C:86]2[C:81](=[CH:82][CH:83]=[CH:84][CH:85]=2)[C:80]2[C:75]1=[CH:76][CH:77]=[CH:78][CH:79]=2)=[O:71])[C@H:41](C(O)=O)[CH2:42][CH2:43][CH2:44][NH:45][C:46](=[NH:66])[NH:47][S:48]([C:51]1[C:64]([CH3:65])=[C:62]([CH3:63])[C:61]2[O:60][C:57]([CH3:59])([CH3:58])[CH2:56][CH2:55][C:54]=2[C:52]=1[CH3:53])(=[O:50])=[O:49].CCN=C=NCCCN(C)C.CN1CCOCC1>CN(C=O)C.C1COCC1.C(OCC)C>[NH:40]([C:70]([O:72][CH2:73][CH:74]1[C:86]2[C:81](=[CH:82][CH:83]=[CH:84][CH:85]=2)[C:80]2[C:75]1=[CH:76][CH:77]=[CH:78][CH:79]=2)=[O:71])[C@H:41]([C:13]([N:1]1[CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([NH:5][CH2:6][C:7]([NH2:9])=[O:8])=[O:4])=[O:15])[CH2:42][CH2:43][CH2:44][NH:45][C:46](=[NH:66])[NH:47][S:48]([C:51]1[C:64]([CH3:65])=[C:62]([CH3:63])[C:61]2[O:60][C:57]([CH3:58])([CH3:59])[CH2:56][CH2:55][C:54]=2[C:52]=1[CH3:53])(=[O:50])=[O:49]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

12

反応物 8

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7256544Boc-Pro-Gly-NH2HCID 10942334Sodium MethoxideHCID 10953452Ether hydrochloride
HCID 178427573
HCID 178427573、化合物

生成物 1

HCID 178427569HCID 178427569、化合物収率 93.5%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

(See SEQUENCE ID NO: 10) 540 mg (2.0 mmol) of Boc-Pro-Gly-NH2 are dissolved in 5 ml abs. THF and mixed while stirring with 3 ml HCl/diethyl ether (abs. diethyl ether is for this saturated with hydrogen chloride at 0° C.). After 0.5 hours the solvent is removed under vacuum and co-evaporated three times with 5 ml toluene on each occasion. 110 mg (2.0 mmol) NaOMe are added to 5 ml abs. THF and after 5 min 5 ml DMF, 300 mg (2.0 mmol) HOBT and 1.32 g Fmoc-Arg(Pmc)-OH. Cooling to -10° C. takes place, 600 mg (3 mmol) EDCI are added and a pH of 7.0 is set with 0.33 ml NMM. After 15 hours of stirring the solvent is removed under vacuum, the resulting syrup absorbed in 150 ml ethyl acetate and the organic phase washed three times with 10 ml 0.5 N HCl, 10% NaHCO3 solution and H2O respectively. The organic phase is dried with MgSO4, the solvent distilled off under vacuum and the product precipitated from hexane. 1.52 g (93%) of thin-layer chromatographically identical Fmoc-Arg(Pmc)-Pro-Gly-NH2 are obtained as a colourless powder.

後処理

  1. dissolutionare dissolved in 5 ml abs
  2. customat 0° C.
  3. customAfter 0.5 hours the solvent is removed under vacuum
  4. additionare added
  5. customis removed under vacuum
  6. customthe resulting syrup absorbed in 150 ml ethyl acetate
  7. washthe organic phase washed three times with 10 ml 0.5 N HCl, 10% NaHCO3 solution and H2O respectively
  8. dry with materialThe organic phase is dried with MgSO4
  9. distillationthe solvent distilled off under vacuum
  10. customthe product precipitated from hexane

出典と根拠

ORDレコード
ord-5413d16f89ec4ca6bf43e7328d0cc330
出典データセット
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05556836

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート