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Trifluoroacetic acid → (4S,5R)-7-((R)-2-amino-4-phenoxybutanoyl)-2-methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one

HRID 1036697
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HRID 1036697 반응식
[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C@@:4]2([CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:37])[C@H:19]([NH:29]C(=O)OC(C)(C)C)[CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:13]2)[C:3]1=[O:38].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:29][C@H:19]([CH2:20][CH2:21][O:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:18]([N:14]1[CH2:15][CH2:16][CH2:17][C@:4]2([C:3](=[O:38])[N:2]([CH3:1])[CH2:6][C@H:5]2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)=[O:37]
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86674100Tert-butyl (R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-ylcarbamate

생성물 1

HCID 71060207(4S,5R)-7-((R)-2-amino-4-phenoxybutanoyl)-2-methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Tert-butyl (R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-ylcarbamate (242 mg; 0.464 mmol) was solubilised in DCM (1 ml). TFA (0.894 ml; 11.60 mmol) was added and the solution stirred at RT for 20 minutes before being concentrated in vacuo. The residual oil was dissolved with methanol (3 ml) and passed through a 10 g SCX-2 cartridge eluting with 2M NH3 in methanol (70 ml). The solvent was removed in vacuo yielding (4S,5R)-7-((R)-2-amino-4-phenoxybutanoyl)-2-methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one.

후처리

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe residual oil was dissolved with methanol (3 ml)
  3. washeluting with 2M NH3 in methanol (70 ml)
  4. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-f1d5ee736ae149c6bb7e32d7daa66c29
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546416B2

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