4-Methylmorpholine → 2-Tert-butoxycarbonylamino-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester

HRID 2038998ノート

反応式

HRID 2038998 の反応式
CN1CCOCC1.[CH2:8]([O:15][C:16](=[O:31])[CH:17]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:19][C:20]([OH:22])=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN([C:35]([O:39][N:40]1N=NC2C=CC=N[C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CNOC>CN(C)C=O>[CH2:8]([O:15][C:16](=[O:31])[CH:17]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:19][C:20](=[O:22])[N:40]([O:39][CH3:35])[CH3:41])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3255276Boc-D-glutamic acid 1-benzyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 731946592-Tert-butoxycarbonylamino-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester収率 100.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Methylmorpholine (9.77 mL, 88.9 mmol) was added to a suspension of 2-tert-butoxycarbonylamino-pentanedioic acid 1-benzyl ester (6 g, 17.7 mmol), and HATU (8.11 g, 21.3 mmol) in dimethylformamide (20 mL). After 5 minutes N,O-dimethylhydroxylamine hydrochloride (2.60 g, 26.7 mmol), was added to the solution. After 1 hour the solvent was removed under reduced pressure. The residue was taken up in ethyl acetate (150 mL), and washed with water (100 mL), aqueous hydrogen chloride (0.5 N, 2×100 mL), saturated sodium bicarbonate (100 mL), and saturated sodium chloride (100 mL). The organic phase was dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was subjected to flash chromatography with eluent of ethyl acetate and hexane. The product-containing fractions were combined and the solvent was removed under reduced pressure to yield 2-tert-butoxycarbonylamino-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester (6.8 g, 17.8 mmol, 99%). C19H28N2O6 calculated 380.2 observed [M+1]+ 381.2; rt=2.48 min.

後処理

  1. additionwas added to the solution
  2. customAfter 1 hour the solvent was removed under reduced pressure
  3. washwashed with water (100 mL), aqueous hydrogen chloride (0.5 N, 2×100 mL), saturated sodium bicarbonate (100 mL), and saturated sodium chloride (100 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-6d0bb5433e1e43be82059de014071436
出典データセット
uspto-grants-2013_11
特許番号
US08575118B2

反応ノート

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