Dimethylformamide → HCID 86671822、化合物

HRID 2038796ノート

反応式

HRID 2038796 の反応式
C(C1CCC1(N)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.CN([C:19]([O:23][N:24]1N=NC2C=CC=N[C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CN[O:43][CH3:44].[CH:45](N(C(C)C)CC)([CH3:47])[CH3:46].C[N:55]([CH:57]=[O:58])[CH3:56]>CCOC(C)=O.O>[C:4]([O:3][C:57](=[O:58])[NH:55][C:56]1([C:44](=[O:43])[N:24]([O:23][CH3:19])[CH3:25])[CH2:47][CH2:45][CH2:46]1)([CH3:5])([CH3:6])[CH3:7]

参加物

8

反応物 5

HCID 6228DimethylformamideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67516526HCID 67516526、化合物

生成物 1

HCID 86671822HCID 86671822、化合物収率 99%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Boc-1-aminocyclobutane-1-carboxylic acid (10.0 g, 45.1 mmol), HATU (20.5 g, 54.1 mmol) and N,O-dimethylhydroxylamine hydrochloride (4.93 g, 49.6 mmol) were combined in DMF (100 mL). To this solution was added diisopropylethylamine (31.4 mL, 180.3 mmol). The reaction was stirred for 2 h, diluted with EtOAc and poured into H2O. The aqueous phase was separated and extracted two more times with EtOAc. The organic layers were combined and washed with brine, dried (Na2SO4), decanted and concentrated in vacuo. The resultant solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane) to afford [1-(methoxy-methyl-carbamoyl)-cyclobutyl]-carbamic acid tert-butyl ester as a white solid (11.5 g, 99%).

後処理

  1. customThe aqueous phase was separated
  2. extractionextracted two more times with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customdecanted
  6. concentrationconcentrated in vacuo
  7. customThe resultant solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane)

出典と根拠

ORDレコード
ord-4fb7dd28c12f48f2871c4ddbd9efd407
出典データセット
uspto-grants-2013_11
特許番号
US08575360B2

反応ノート

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