N-(tert-butoxycarbonyl)glycine → ((2S,4R)-4-(2-aminoacetamido)-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate

HRID 655981

反応式

HRID 655981 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:30])[O:11][CH2:12][C@@H:13]2[CH2:17][C@@H:16]([NH2:18])[CH2:15][N:14]2[C:19](=[O:29])[NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[CH:5][CH:4]=1)[CH3:2].[NH:31](C(OC(C)(C)C)=O)[CH2:32][C:33](O)=[O:34].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:30])[O:11][CH2:12][C@@H:13]2[CH2:17][C@@H:16]([NH:18][C:33](=[O:34])[CH2:32][NH2:31])[CH2:15][N:14]2[C:19](=[O:29])[NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[CH:5][CH:4]=1)[CH3:2]

参加物

5

反応物 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59778486((2S,4R)-4-amino-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate

生成物 1

HCID 25026415((2S,4R)-4-(2-aminoacetamido)-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate収率 54.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of ((2S,4R)-4-amino-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate (60 mg, 0.14 mmol) in DMF were added Boc-Gly-OH (37 mg, 0.21 mmol) and HBTU (80 mg, 0.21 mmol). The reaction mixture was stirred at rt overnight and purified on RP-HPLC using a mixture of acetonitrile and H2O. The fraction containing the product was combined and concentrated. The residue was dissolved in MeOH and 4N HCl in dioxane. The reaction mixture was stirred at rt for 1 h and concentrated to give ((2S,4R)-4-(2-aminoacetamido)-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate (37 mg, 51%). LRMS (M+H+) m/z 488.1.

後処理

  1. custompurified on RP-HPLC
  2. additiona mixture of acetonitrile and H2O
  3. additionThe fraction containing the product
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in MeOH
  6. stirringThe reaction mixture was stirred at rt for 1 h
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-d201994f44bb495cb3f625e6f9650642
出典データセット
uspto-grants-2011_12
特許番号
US08071625B2

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