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Methanol → tert-Butyl 4-(5-(tert-butoxycarbonylamino)-2-chloro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate

HRID 1808894
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HRID 1808894 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH:12]=[CH:13][C:14]=1[C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C1C(=O)N([Cl:46])C(=O)C1.CO>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]([Cl:46])=[C:11]([N:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]2)[CH:10]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]
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6

반응물 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 31398ChlorosuccinimideHCID 66695921tert-Butyl 4-(3-(tert-butoxycarbonylamino)-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate

생성물 1

HCID 66692185tert-Butyl 4-(5-(tert-butoxycarbonylamino)-2-chloro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of tert-butyl 4-(3-(tert-butoxycarbonylamino)-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate (360 mg, 0.827 mmol) in DCM (4 mL) at −78° C. was added TFA (0.064 mL, 0.827 mmol). The reaction mixture was warmed to 0° C., followed by the addition of NCS (110 mg, 0.827 mmol) and MeOH (2.000 mL). The resulted reaction mixture was stirred at RT for 16 hours. The product was purified by flash chromatography (2% EtOAc/DCM, Rf 0.50) to give 150 mg (77% yield) of tert-Butyl 4-(5-(tert-butoxycarbonylamino)-2-chloro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate. 1H-NMR (CDCl3, 400 MHz): δ 10.31 (1H, s), 8.18 (1H, s), 7.98 (1H, s), 3.90 (3H, s), 3.61 (4H, t, J=4.8 Hz), 3.14 (4H, t, J=4.8 Hz), 1.53 (9H, s), 1.49 (9H, s).

후처리

  1. customThe resulted reaction mixture
  2. customThe product was purified by flash chromatography (2% EtOAc/DCM, Rf 0.50)

출처 및 근거

ORD 기록
ord-dcd72454d8ac4e039200edd358a050e8
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362004B2

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