4-Methylmorpholine → tert-butyl (2S)-1-((1S,3aR,6aS)-1-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)hexahydrocyclopenta-[c]pyrrol-2(1H)-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

HRID 424973ノート

反応式

HRID 424973 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:10]([N:12]1[CH2:16][C@@H:15]2[CH2:17][CH2:18][CH2:19][C@@H:14]2[C@H:13]1[C:20](O)=[O:21])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[NH2:55][C@@H:56]([CH2:65][CH2:66][CH3:67])[CH:57]([OH:64])[C:58]([NH:60][CH:61]1[CH2:63][CH2:62]1)=[O:59].Cl.N[C@@H](CCC)C(O)C(NC1CC1)=O>ClCCl.CN(C)C=O.O>[CH:61]1([NH:60][C:58](=[O:59])[CH:57]([OH:64])[C@@H:56]([NH:55][C:20]([C@@H:13]2[C@H:14]3[CH2:19][CH2:18][CH2:17][C@H:15]3[CH2:16][N:12]2[C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:65][CH2:66][CH3:67])[CH2:63][CH2:62]1

参加物

10

反応物 6

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 23634853(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 59677749(1S,3aR,6aS)-2-((S)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acidHCID 66656935Hexanamide, 3-amino-N-cyclopropyl-2-hydroxy-, hydrochloride (1:1), (3S)-

生成物 1

HCID 57930532tert-butyl (2S)-1-((1S,3aR,6aS)-1-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)hexahydrocyclopenta-[c]pyrrol-2(1H)-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

The crude (1S,3aR,6aS)-2-((S)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid from Example 10 was dissolved in dichloromethane (4 mL) and treated with 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (EDCI) (71 mg, 2 eq), 1-hydroxybenzotriazole (HOBT) (57 mg, 2 eq) and N-methyl morpholine (0.2 mL, 5 eq) at room temperature. To this mixture was added after 30 minutes (3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide, the compound of formula (12) (1 eq) in dichloromethane (3 mL) and N,N-dimethylformamide (3 mL) and the reaction mixture was stirred at room temperature. After 18 hours the reaction mixture was diluted with water, and the product extracted into ethyl acetate. The organic extract was washed with brine, dried and evaporated to dryness under reduced pressure, to give crude tert-butyl (2S)-1-((1S,3aR,6aS)-1-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)hexahydrocyclopenta-[c]pyrrol-2(1H)-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate, the compound of formula (17).

後処理

  1. extractionthe product extracted into ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. customdried
  5. customevaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-9396a053a37e483d8d6635c38edf50fa
出典データセット
uspto-grants-2012_01
特許番号
US08106059B2

反応ノート

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