Hydrochloric Acid → 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

HRID 2245214

反応式

HRID 2245214 の反応式
[N:1]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([NH:5][C@H](C(N)=O)C(C)C)=[O:4].Cl.[CH2:24]1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N([OH:48])N=NC=2C=1>>[N:1]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([OH:4])=[O:48].[NH:1]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@H:2]([C:3]([NH2:5])=[O:4])[CH:13]([CH3:14])[CH3:24]

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 11141514Boc-Pro-Val-NH22 回HCID 21712060DCCI HOBt

生成物 2

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 11241393Boc-L-valine amide

実験手順

In such a synthesis, the lysine side chain is protected by a MSOC protective group introduced onto Boc-Lys-OH so as to form Boc-Lys(MSOC)-OH. The diprotected N(α),N(ε) lysine is coupled with Boc-Pro-Val-NH2, HCl by the conventional DCC/HOBt method. The Boc-Pro-Val-NH2, HCl reactant is in turn obtained in two steps from Boc-Pro-OH and Boc-Val-NH2. The overall yield is 33% calculated based on Boc-Lys(MSOC)-OH. The global synthesis scheme is illustrated in the scheme (I) hereunder:

出典と根拠

ORDレコード
ord-17fef5a278f94ff5bdd2b8d751b0c84a
出典データセット
uspto-grants-2010_03
特許番号
US07683026B2

関連ノート

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