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 424973노트

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HRID 424973 반응식
[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

참가 물질

10

반응물 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)-

생성물 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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9396a053a37e483d8d6635c38edf50fa
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106059B2

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