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

HRID 437689

Reaction equation

HRID 437689 reaction equation
C(OC([NH:8][C@H:9]([C:25]([NH:27][C@@H:28]([C:30]([OH:32])=[O:31])[CH3:29])=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=O)(C)(C)C.C(O[C:38]([NH:40][C@@H:41]([C:51]([OH:53])=O)[CH2:42][O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:39])(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1.[C:69]([O:73][C:74]([NH:76][C@H:77](C(O)=O)[CH2:78][C:79]1[C:87]2[C:82](=[CH:83][CH:84]=[CH:85][CH:86]=2)[NH:81][CH:80]=1)=[O:75])([CH3:72])([CH3:71])[CH3:70]>>[C:69]([O:73][C:74]([NH:76][C@H:77]([C:38]([NH:40][C@@H:41]([C:51]([NH:8][C@H:9]([C:25]([NH:27][C@@H:28]([C:30]([OH:32])=[O:31])[CH3:29])=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:53])[CH2:42][O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:39])[CH2:78][C:79]1[C:87]2[C:82](=[CH:83][CH:84]=[CH:85][CH:86]=2)[NH:81][CH:80]=1)=[O:75])([CH3:72])([CH3:70])[CH3:71]

Participants

5

Reactant 4

HCID 10868Dicyclohexylcarbodiimide2×HCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 2733693(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acidHCID 12876484Nalpha-t-butoxycarbonyl-O-benzyl-L-tyrosyl-D-alanine

Product 1

HCID 86734883Nalphat-Butoxycarbonyl-L-tryptophyl-O-benzyl-D-seryl-O-benzyl-L-tyrosyl-D-alanine

Conditions

Temperature
25 °C

Procedure

Nαt-Butoxycarbonyl-L-tryptophyl-O-benzyl-D-seryl-O-benzyl-L-tyrosyl-D-alanine resin is prepared from 8 g. of Nα-t-butoxycarbonyl-O-benzyl-L-tyrosyl-D-alanine resin by successive coupling, according to the general process for solid phase synthesis given in Example 1, with (13 g., 9.8 mmol, of Nα-t-butoxycarbonyl-O-benzyl-D-serine and 2 g., 9.7 mmol, of dicyclohexylcarbodiimide and (2) 3 g., 9.8 mmol, of Nα-t-butoxycarbonyl-L-tryptophan and 2 g. of dicyclohexylcarbodiimide. The resin is washed with ethanol and dried. It is then stirred for twenty-four hours at 25° C. with 200 ml. of methanol and 20 ml. of triethylamine. The mixture is filtered and the methanol solution evaporated. The residue is solidified from ether-petroleum ether; 2 g.; m.p. 155°-156° C.

Workup

  1. washThe resin is washed with ethanol
  2. customdried
  3. filtrationThe mixture is filtered
  4. customthe methanol solution evaporated

Sources & evidence

ORD record
ord-7e5c7cd0664f4808bd5f2344c1495cfb
Source dataset
uspto-grants-1977_06
Patent number
US04031069

Linked notes

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