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1,2-Dichloroethane → Tert-butyl 3-(n-[(1r)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)amino]phenyl}piperidyl)-2-oxoethyl]carbamoyl)azetidine-carboxylate

HRID 489666
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HRID 489666 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:33][C:34](OC(C)(C)C)=[O:35])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]([CH2:29][CH:30]3[CH2:32][CH2:31]3)[S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:62]([N:69]1[CH:72](C(O)=O)[CH2:71][CH2:70]1)([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63]>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:33][C:34]([CH:71]2[CH2:70][N:69]([C:62]([O:64][C:65]([CH3:66])([CH3:67])[CH3:68])=[O:63])[CH2:72]2)=[O:35])[C:10]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]([CH2:29][CH:30]3[CH2:32][CH2:31]3)[S:25]([CH3:28])(=[O:27])=[O:26])[CH2:16][CH2:17]2)=[O:11])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 36238861-[(Tert-butoxy)carbonyl]azetidine-2-carboxylic acidHCID 23587431n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)amino]phenyl}-piperidyl)-2-oxoethyl](tert-butoxy)carboxamide

생성물 1

HCID 23587442
Tert-butyl 3-(n-[(1r)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)amino]phenyl}piperidyl)-2-oxoethyl]carbamoyl)azetidine-carboxylate
수율 71.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

The title compound was prepared according to the procedure described in Example 11 (Step c) using N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)amino]phenyl}-piperidyl)-2-oxoethyl](tert-butoxy)carboxamide (Example 11 Step b) (450 mg, 0.76 mmol) and 50% TFA in CH2Cl2 (6 mL) followed by EDC (Aldrich) (259 mg, 1.35 mmol), HOBT (Aldrich) (270 mg, 2.0 mmol) and N-Boc-azetidine-4-carboxylic acid (PepTech Corporation) (220 mg, 1.1 mmol) in THF (20 mL). Purification by silica gel chromatography (10:25:65 MeOH:EtOAc:hexane) provided the title compound as a white foam (365 mg). MS (ESI, pos. ion) m/z: 673 (M+1); (ESI, neg. ion) m/z: 671 (M−1). Calc'd for C34H45ClN4O6S: 673.26.

후처리

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (10:25:65 MeOH:EtOAc:hexane)

출처 및 근거

ORD 기록
ord-8746b430bf9f4b8f81ac8b0fbb41dda6
출처 데이터셋
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06977264B2

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