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 25226

反応式

HRID 25226 の反応式
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]

参加物

5

反応物 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

生成物 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 ester収率 100.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)].

後処理

  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

出典と根拠

ORDレコード
ord-f7728dba6d914712bcbba69d5d6eacf8
出典データセット
uspto-grants-2005_02
特許番号
US06858603B2

関連ノート

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