Triethylamine → N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester

HRID 1198096

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HRID 1198096 반응식
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[CH2:22]([O:29][C:30]([NH:32][C@H:33]([C:38](O)=[O:39])[CH2:34][C:35]([OH:37])=[O:36])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.COC(=O)[C@H](CC1C=CC=CC=1)N.Cl.C(N(CC)CC)C>C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[K+].[K+].[K+].C(OCC)(=O)C.OCC(CO)O>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:38](=[O:39])[C@H:33]([CH2:34][C:35](=[O:36])[OH:37])[NH:32][C:30]([O:29][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:31]

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 736234L-Phenylalanine, methyl esterHCID 2723942N-(Benzyloxycarbonyl)aspartic acid2회

생성물 1

HCID 10159630N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester

시약·촉매·용매 3

HCID 753Glycerol용매HCID 8857Ethyl Acetate용매3회HCID 13344Tripotassium citrate용매

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온도
25 °C

실험 절차

Papain (1 g; obtained from J. E. Siebel Son's Co.) was well suspended in 2 ml of 3.0M potassium citrate buffer (pH 5.1), the suspension was then mixed with 2 ml of glycerol. To 100 ml of ethyl acetate, 80 mmole of L-phenylalanine methyl ester hydrochloride and 80 mmole of triethylamine were added and stirred at 25° C. for 40 min then 40 mmole of N-benzyloxycarbonyl-L-aspartic acid was added and stirred for 20 min. The whole ethyl acetate mixture, containing soluble L-phenylalanine methyl ester and N-benzyloxycarbonyl-L-aspartic acid and insoluble triethylamine hydrochloride, w-as subsequently added to the papain suspension. The reaction mixture was stirred at 25° C. for 22 hr then 200 ml of ethyl acetate was added and stirred at 55° C. for 15 min and filtered. As determined by HPLC analysis the yield of the N-benzyloxycarbonyl-α-L-aspartyl-L-phenylalanine methyl ester in the filtrate was 85% calculated on the basis of the initial amount of the N-benzyloxycarbonyl-L-aspartic acid. The ethyl acetate solution was then extracted twice with 150 ml of 0.01M phosphate buffer (pH 7.0), then twice with 150 ml of 0.3N hydrochloric acid. The final organic layer was dehydrated with 10 g of anhydrous Na2SO4, then evaporated and vacuum dried to give 17.4 partially purified N-benzyloxycarbonyl-α-L-aspartyl-L-phenylalanine methyl ester.

후처리

  1. stirringstirred for 20 min
  2. additionw-as subsequently added to the papain suspension
  3. stirringThe reaction mixture was stirred at 25° C. for 22 hr
  4. stirringstirred at 55° C. for 15 min
  5. filtrationfiltered
  6. extractionThe ethyl acetate solution was then extracted twice with 150 ml of 0.01M phosphate buffer (pH 7.0)
  7. customevaporated
  8. customvacuum dried

출처 및 근거

ORD 기록
ord-9abbc20bb3394dd6b256eefba4c6e34d
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05279946

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