Dicyclohexylamine → BOC-Nva-Met-OMe

HRID 851721

反応式

HRID 851721 の反応式
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH2:3][CH2:4][CH3:5].C1CCC(NC2CCCCC2)CC1.[NH2:29][C@H:30]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:32][S:33][CH3:34].Cl.C(N(CC)CC)C.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)(Cl)Cl>[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([NH:29][C@H:30]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:8])[CH2:3][CH2:4][CH3:5]

参加物

7

反応物 5

HCID 7582DicyclohexylamineHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2733748(2S)-2-(((tert-butoxy)carbonyl)amino)pentanoic acidHCID 11435579L-Methionine, methyl ester, hydrochloride

生成物 1

HCID 57129312BOC-Nva-Met-OMe収率 71%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

BOC-Nva-OH, liberated from 4.78 g (12 mmoles) of the DCHA salt as described in Step 1 of Example 4, and 2.6 g (13 mmoles) of H-Met-OMe.HCl are dissolved in 40 ml of chloroform, and 1.82 ml (13 mmoles) of triethylamine are added. The mixture is cooled with ice, and a solution of 2.58 g (12.5 mmoles) of DCC in 20 ml of chloroform is added under stirring. The reaction mixture is allowed to stand at 5° C. overnight, thereafter the separated DCU is filtered off. The filtrate is washed thrice with 20 ml of n hydrochloric acid, each, thrice with 20 ml of n sodium hydrocarbonate solution, each, and then with 20 ml of water, dried over anhydrous sodium sulfate, and evaporated. The oily residue is crystallized from petroleum ether, and the resulting 3.42 g of crude product is recrystallized from a mixture of ethyl acetate and petroleum ether. 3.08 g (71%) of BOC-Nva-Met-OMe are obtained; m.p.: 69°- 70° C., Rf2 =0.81, [α]D25 =-42.7° (c=1%, in methanol).

後処理

  1. temperatureThe mixture is cooled with ice
  2. filtrationthe separated DCU is filtered off
  3. washThe filtrate is washed thrice with 20 ml of n hydrochloric acid
  4. dry with materialeach, thrice with 20 ml of n sodium hydrocarbonate solution, each, and then with 20 ml of water, dried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe oily residue is crystallized from petroleum ether
  7. customthe resulting 3.42 g of crude product is recrystallized from a mixture of ethyl acetate and petroleum ether

出典と根拠

ORDレコード
ord-a436c9f484834bf091c7315974f2dd90
出典データセット
uspto-grants-1983_05
特許番号
US04386073

関連ノート

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