Dicyclohexylcarbodiimide → Nalpha-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-alanine

HRID 437688

반응식

HRID 437688 반응식
C(OC([NH:8][C@@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=O)(C)(C)C.C(O[C:19]([NH:21][C@H:22]([C:38]([OH:40])=O)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)=[O:20])(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1.C(O[C:61]([NH:63][C@H:64](C(O)=O)[CH2:65][O:66][CH2:67][C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1)=[O:62])(C)(C)C.[C:77]([O:81][C:82]([NH:84][C@H:85](C(O)=O)[CH2:86][C:87]1[C:95]2[C:90](=[CH:91][CH:92]=[CH:93][CH:94]=2)[NH:89][CH:88]=1)=[O:83])([CH3:80])([CH3:79])[CH3:78]>C(N(CC)CC)C.CO>[C:77]([O:81][C:82]([NH:84][C@H:85]([C:61]([NH:63][C@H:64]([C:19]([NH:21][C@H:22]([C:38]([NH:8][C@@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:40])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:28][CH:29]=1)=[O:20])[CH2:65][O:66][CH2:67][C:68]1[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=1)=[O:62])[CH2:86][C:87]1[C:95]2[C:90](=[CH:91][CH:92]=[CH:93][CH:94]=2)[NH:89][CH:88]=1)=[O:83])([CH3:78])([CH3:79])[CH3:80]

참가 물질

8

반응물 5

HCID 10868Dicyclohexylcarbodiimide3회HCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 637606BOC-D-alanine

생성물 1

HCID 53959304Nalpha-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-alanine

시약·촉매·용매 2

HCID 887Methanol용매HCID 8471Triethylamine용매

실험 절차

Nα-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-alanine resin is prepared from 23 g., 14 mmol. of Nα-t-butoxycarbonyl-D-alanine resin by successive coupling, according to the general process for solid phase synthesis given in Example 1 with (1) 7 g., 19 mmol, of Nα-t-butoxycarbonyl-O-benzyl-L-tyrosine and 4 g., 19.4 mmol, of dicyclohexylcarbodiimide, (2) 6 g., 19.7 mmol, of Nα-t-butoxycarbonyl-O-benzyl-L-serine and 4 g. of dicyclohexylcarbodiimide, and (3) 6 g., 19.7 mmol, of Nα-t-butoxycarbonyl-L-tryptophan and 4 g. of dicyclohexylcarbodiimide. The resin thus obtained, 30 g., is stirred for 20 hours with 600 ml. of methanol and 50 ml. of triethylamine. The solution is filtered and evaporated. The residue is solidified by trituration in ether; 8 grams; m.p. 93°-94° C.

후처리

  1. customThe resin thus obtained
  2. filtrationThe solution is filtered
  3. customevaporated

출처 및 근거

ORD 기록
ord-802c40f114c1414983a6b7b924a20ec2
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04031069

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