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

HRID 437688

Reaction equation

HRID 437688 reaction equation
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]

Participants

8

Reactant 5

HCID 10868Dicyclohexylcarbodiimide3×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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-802c40f114c1414983a6b7b924a20ec2
Source dataset
uspto-grants-1977_06
Patent number
US04031069

Linked notes

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