N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]hydrazide

HRID 275289

反応式

HRID 275289 の反応式
[CH3:1][C:2]([CH3:13])([O:4][C:5]([NH:7][CH2:8][CH2:9][C:10]([OH:12])=O)=[O:6])[CH3:3].ClC1C=CC2OC3C=CC=CC=3CN(C(O)=O)C=2C=1.[Cl:33][C:34]1[CH:52]=[CH:51][C:37]2[O:38][C:39]3[CH:50]=[CH:49][CH:48]=[CH:47][C:40]=3[CH2:41][N:42]([C:43]([NH:45][NH2:46])=[O:44])[C:36]=2[CH:35]=1.CCN(C(C)C)C(C)C.OS([O-])(=O)=O.[K+]>CN(C=O)C.CCOC(C)=O>[CH3:13][C:2]([CH3:1])([O:4][C:5]([NH:7][CH2:8][CH2:9][C:10]([NH:46][NH:45][C:43]([N:42]1[CH2:41][C:40]2[CH:47]=[CH:48][CH:49]=[CH:50][C:39]=2[O:38][C:37]2[CH:51]=[CH:52][C:34]([Cl:33])=[CH:35][C:36]1=2)=[O:44])=[O:12])=[O:6])[CH3:3]

参加物

8

反応物 5

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 516920Potassium bisulfateHCID 135604618-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazideHCID 219834678-chlorodibenz[b,f][1,4]oxazepine-10(11H)carboxylic acid

生成物 1

HCID 152373958-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]hydrazide収率 52%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirring solution of 3.78 g (20 mmol) of N-[(1,1-dimethylethoxy)carbonyl]-β-alanine (6), prepared as described above in Example 6, and 5.79 (20 mmol) of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)carboxylic acid, hydrazine (1), prepared as described above in Example 1, in 50 mL of DMF cooled in an icebath was added 3.5 mL (20 mmol) of DIEA followed by 4.22 g (22 mmol) of N,N-dimethylaminopropylethylcarbodiimide hydrochloride. The reaction was allowed to warm to ambient temperature over a period of 16 hours. To the reaction mixture was added 100 mL of EtOAc and 200 mL of M KHSO4. The layers were separated and then the organic layer was washed with 2×100 mL of M KHSO4, 2×100 mL of a saturated KHCO3 solution, and 100 mL of brine. The organic layer was dried over anhydrous Na2SO4, filtered, and then concentrated in vacuo. The resulting product was purified by column chromatography to yield 4.75 g (52%) of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]hydrazide (7).

後処理

  1. customprepared
  2. temperaturecooled in an icebath
  3. customThe layers were separated
  4. washthe organic layer was washed with 2×100 mL of M KHSO4, 2×100 mL of a saturated KHCO3 solution, and 100 mL of brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting product was purified by column chromatography

出典と根拠

ORDレコード
ord-ab2d8c0609164b65843aeb37c7797482
出典データセット
uspto-grants-1995_02
特許番号
US05393747

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