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

HRID 437688

反応式

HRID 437688 の反応式
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]

参加物

8

反応物 5

HCID 10868Dicyclohexylcarbodiimide3 回HCID 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-802c40f114c1414983a6b7b924a20ec2
出典データセット
uspto-grants-1977_06
特許番号
US04031069

関連ノート

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