Diisopropylethylamine → 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

HRID 446958

反応式

HRID 446958 の反応式
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:16]([OH:18])=O)[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:52][O:53][C:54]([CH:56]1[CH2:60][N:59]([C:61]([O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[O:62])[CH:58]2[CH2:71][CH2:72][NH:73][CH:57]12)=[O:55]>CN1C(=O)CCC1.CCOC(C)=O>[CH3:52][O:53][C:54]([CH:56]1[CH2:60][N:59]([C:61]([O:63][CH2:64][C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)=[O:62])[CH:58]2[CH2:71][CH2:72][N:73]([C:16](=[O:18])[CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[CH:57]12)=[O:55]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 7004938N-(tert-Butoxycarbonyl)-L-cyclohexylglycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67281633HCID 67281633、化合物

生成物 1

HCID 672814894-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester収率 106.3%

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 Boc-L-cyclohexylglycine (257 mg, 1 mmol) in NMP (5 mL) was cooled to 0° C. and treated with HATU (380 mg, 1 mmol) followed by DIPEA (0.3 mL, 1.7 mmol). After 10 min, 15 (309 mg, 1.0 mmol) in NMP (5 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 to afford 16 as an orange-colored foam (578 mg) which was used without further purification. Mass spectrum, m/z [544.4] (M+H)+.

後処理

  1. washwashed successively with 1M HCl, saturated NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-a34612f279514ad5b5d29c3cc47dcaac
出典データセット
uspto-grants-2013_07
特許番号
US08481495B2

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