Methylamine → HCID 86670469, 화합물

HRID 1911853노트

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HRID 1911853 반응식
CN.[C:3]([O:7][C:8]([N:10]1[C@@H:14]([C@H:15]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][CH2:12][C@H:11]1[CH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:40][N:41](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.C1COCC1>[Si:23]([O:22][C@H:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:14]1[CH2:13][CH2:12][C@@H:11]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:35](=[O:36])[NH:41][CH3:40])=[CH:38][CH:39]=2)[N:10]1[C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])([C:26]([CH3:28])([CH3:29])[CH3:27])([CH3:24])[CH3:25]

참가 물질

8

반응물 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67971935HCID 67971935, 화합물

생성물 1

HCID 86670469HCID 86670469, 화합물수율 59%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Methylamine (5.71 mL of a 2M THF solution, 11.4 mmol) was added to a stirred, room temperature solution of 4-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)benzoic acid (2.00 g, 3.80 mmol), HATU (1.736 g, 4.56 mmol, 1.2 equivalents) and DIPEA (3.32 mL, 19.0 mmol, 5 equivalents) in DMF (7.8 mL). The reaction was stirred at room temperature for 12 hours, after which the mixture was diluted with EtOAc and partitioned with water. The aqueous layer was extracted with EtOAc (3×), and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by normal phase flash chromatography using silica gel (0-50% hexanes/ethyl acetate). The product fractions were collected and concentrated in vacuo to afford the title compound as a white solid (1.20 g, 59%). LC-MS=561.2 (M+Na)+.

후처리

  1. custompartitioned with water
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by normal phase flash chromatography
  8. customThe product fractions were collected
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-484b98469d50470895a1e58bba4d9704
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604038B2

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