Nitric Acid → L-Alanyl-L-Glutamine

HRID 1373726노트

반응식

HRID 1373726 반응식
C(C([NH:7][C@H:8]([C:10](O)=[O:11])[CH3:9])=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl.[NH2:40][C@H:41]([C:47]([OH:49])=[O:48])[CH2:42][CH2:43][C:44](=[O:46])[NH2:45].[OH-].[K+].[N+]([O-])(O)=O>ClCCCl.CCOCC.C1CCCCC1.O>[NH2:7][C@H:8]([C:10]([NH:40][C@H:41]([C:47]([OH:49])=[O:48])[CH2:42][CH2:43][C:44](=[O:46])[NH2:45])=[O:11])[CH3:9]

참가 물질

11

반응물 6

HCID 944Nitric AcidHCID 5961L-GlutamineHCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 42254381(S)-N-tert-butylcarbonylalanine

생성물 1

HCID 123935L-Alanyl-L-Glutamine수율 40%

시약·촉매·용매 4

HCID 111,2-Dichloroethane용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8078Cyclohexane용매

실험 절차

In a round bottom flask, add in 10 mmol of tert-butylcarbonylalanine (Boc-Ala), 15 mmol of triphenyl phosphine and 20 mmol of hexachloroethane, and then add in 20 ml of 1,2-dichloroethane. After reacting at 10° C. for 20 min, drop it into a liquid mixture containing 30 mmol glutamine, 20 ml of water and 20 ml of cyclohexane. While reacting, regulate pH to 11 with potassium hydroxide, the reaction temperature is 20° C., the reaction time after dropping is 30 min. And then acidify it to regulate pH=1.5 with dilute nitric acid. The aqueous phase, after concentrated, reacts with trifluoroacetic acid at room temperature for 15 hours. As the reaction is finished, add in 50 ml of ether, solids deposit, the product L-Ala-L-Gln with a yield of 40% is obtained by recrystallizing the solids with tetrahydrofuran-water.

후처리

  1. customis 20° C.
  2. waitthe reaction time after dropping is 30 min
  3. concentrationThe aqueous phase, after concentrated
  4. customreacts with trifluoroacetic acid at room temperature for 15 hours

출처 및 근거

ORD 기록
ord-fd5f25d28fb44971983842af9cd27cd5
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163917B2

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