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4-Methylmorpholine → 4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

HRID 446988
ノート
印刷プレビュー

反応式

HRID 446988 の反応式
[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([OH:5])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[C:47]([O:51][C:52]([N:54]1[CH2:58][CH2:57][CH:56]2[NH:59][CH2:60][CH:61]([C:62](=[O:74])[NH:63][C:64]3[C:73]4[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=4)[CH:67]=[CH:66][CH:65]=3)[CH:55]12)=[O:53])([CH3:50])([CH3:49])[CH3:48]>CN1C(=O)CCC1.CCOC(C)=O>[C:47]([O:51][C:52]([N:54]1[CH2:58][CH2:57][CH:56]2[N:59]([C:3](=[O:5])[CH2:2][NH:1][C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])[CH2:60][CH:61]([C:62](=[O:74])[NH:63][C:64]3[C:73]4[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=4)[CH:67]=[CH:66][CH:65]=3)[CH:55]12)=[O:53])([CH3:50])([CH3:48])[CH3:49]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672813746-(Naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 67281528
4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester
収率 73.5%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

実験手順

A solution of Cbz-Gly-OH (250 mg, 1.20 mmol) in NMP (2 mL) was cooled to 0° C. and treated with HATU (502 mg, 1.32 mmol) followed by NMM (0.2 mL). After 10 min, 54 (360 mg, 0.95 mmol) in NMP (2 mL) was added. The reaction mixture was allowed to warm to ambient temperature overnight. The solution was diluted with EtOAc, washed successively with 1M HCl, saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated. Purification by reverse phase HPLC (2″ Dynamax® C18, 10-70% ACN in H2O with 0.1% HOAc over 30 min) afforded 55 as a white solid (400 mg). Mass spectrum, m/z [573.2] (M+H)+.

後処理

  1. washwashed successively with 1M HCl, saturated NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by reverse phase HPLC (2″ Dynamax® C18, 10-70% ACN in H2O with 0.1% HOAc over 30 min)

出典と根拠

ORDレコード
ord-deeb4adcd93b4d3b894c69432f1cf3cf
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08481495B2

反応ノート

読み込み中…

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