1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-oxoethyl)-N-methylcarbamic acid tert-butyl ester

HRID 1058832

반응식

HRID 1058832 반응식
CCN=C=NCCCN(C)C.[C:12]([N:19]([CH2:21][C:22]([OH:24])=O)[CH3:20])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([C:54]2[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][CH:55]=2)[N:33]2[CH2:36][C:35](=[CH:37][S:38]([CH2:41][C:42]3[CH:43]=[C:44]([N:48]4[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]4)[CH:45]=[CH:46][CH:47]=3)(=[O:40])=[O:39])[CH2:34]2)=[CH:28][CH:27]=1>ClCCl>[C:15]([O:14][C:12](=[O:13])[N:19]([CH2:21][C:22]([N:51]1[CH2:52][CH2:53][N:48]([C:44]2[CH:45]=[CH:46][CH:47]=[C:42]([CH2:41][S:38]([CH:37]=[C:35]3[CH2:34][N:33]([CH:32]([C:29]4[CH:28]=[CH:27][C:26]([Cl:25])=[CH:31][CH:30]=4)[C:54]4[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][CH:55]=4)[CH2:36]3)(=[O:39])=[O:40])[CH:43]=2)[CH2:49][CH2:50]1)=[O:24])[CH3:20])([CH3:16])([CH3:17])[CH3:18]

참가 물질

5

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 696356951-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine

생성물 1

HCID 69635644(2-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-oxoethyl)-N-methylcarbamic acid tert-butyl ester수율 100.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1.02 g of supported EDCI (5 mM), 47.3 mg of N-Boc-sarcosine and then 10 cm3 of dichloromethane are successively added, at a temperature close to 20° C., to 108.5 mg of 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine. After stirring for 20 hours at a temperature close to 20° C., the reaction mixture is filtered on sintered glass. The resin is rinsed with three times 5 cm3 of dichloromethane. The combined filtrates are washed with 20 cm3 of water, dried over magnesium sulfate, filtered on sintered glass and concentrated to dryness under reduced pressure (1 kPa) at a temperature close to 40° C. 143 mg of (2-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-oxoethyl)-N-methylcarbamic acid tert-butyl ester are thus obtained in the form of a cream-colored lacquer [1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm). A mixture of rotamers is observed at room temperature; 1.31 and 1.41 (2s, 9H in total), 2.78 and 2.81 (2s, 3H in total), 2.93 (2s, 3H), from 3.10 to 3.25 (unresolved complex, 4H), from 3.45 to 3.65 (mt, 4H), 3.80 (mt, 2H), 4.06 and 4.09 (2s, 2H in total), 4.19 (mt, 2H), 4.78 (s, 1H), 6.83 (broad d, J=8 Hz, 1H), 6.93 (broad s, 1H), 7.00 (dd, J=8 and 2.5 Hz, 1H), 7.27 (t, J=8 Hz, 1H), 7.36 (d, J=8 Hz, 4H), 7.46 (d, J=8 Hz, 4H)].

후처리

  1. customclose to 20° C.
  2. filtrationthe reaction mixture is filtered on sintered glass
  3. washThe resin is rinsed with three times 5 cm3 of dichloromethane
  4. washThe combined filtrates are washed with 20 cm3 of water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered on sintered glass
  7. concentrationconcentrated to dryness under reduced pressure (1 kPa) at a temperature
  8. customclose to 40° C

출처 및 근거

ORD 기록
ord-135d51f9ebde45ce90e4fe15a8535870
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518264B2

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