Dicyclohexylcarbodiimide → BOC-Phe-(D)Trp-Lys(Z)-Thr-Cys(MBzl)-Thr-ol

HRID 1903342Notes

Reaction equation

HRID 1903342 reaction equation
[NH:1]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C@H:2]([C:10]([NH:12][C@@H:13]([C:24]([NH:26][C@H:27]([C:43](O)=[O:44])[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1C=CC2N(O)N=NC=2C=1.[NH2:63][C@H:64]([C:68]([NH:70][C@H:71]([C:82]([NH:84][C@H:85]([CH2:89][OH:90])[C@@H:86]([CH3:88])[OH:87])=[O:83])[CH2:72][S:73][CH2:74][C:75]1[CH:81]=[CH:80][C:78]([CH3:79])=[CH:77][CH:76]=1)=[O:69])[C@@H:65]([CH3:67])[OH:66].FC(C(O)=O)(F)F.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CCN(CC)CC>[NH:1]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C@H:2]([C:10]([NH:12][C@@H:13]([C:24]([NH:26][C@H:27]([C:43]([NH:63][C@H:64]([C:68]([NH:70][C@H:71]([C:82]([NH:84][C@H:85]([CH2:89][OH:90])[C@@H:86]([CH3:88])[OH:87])=[O:83])[CH2:72][S:73][CH2:74][C:75]1[CH:76]=[CH:77][C:78]([CH3:79])=[CH:80][CH:81]=1)=[O:69])[C@@H:65]([CH3:67])[OH:66])=[O:44])[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13391310BOC-Phe-(D)Trp-Lys(Z)-OHHCID 131713418H-Thr-Cys(MBzl)-Thr-ol trifluoroacetate

Product 1

HCID 131713420BOC-Phe-(D)Trp-Lys(Z)-Thr-Cys(MBzl)-Thr-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

2.5 ml NEt3, 11.2 g BOC-Phe-(D)Trp-Lys(Z)-OH and 4 g HOBT are added to 9 g H-Thr-Cys(MBzl)-Thr-ol trifluoroacetate in 100 ml DMF. 3.7 g DCCI in 10 ml DMF are added to the solution at -20° C. and the whole is stirred for ca. 18 hours at 0° C. and 2 hrs. at room temperature. Precipitated dicyclohexyl-urea is filtered off and the filtrate concentrated under vacuum and diluted with methanol. H2O is added until the product precipitates. The precipitate is filtered, washed with MeOH/H2O (4:1) and dried to yield the title compound:

Workup

  1. customat room temperature
  2. filtrationPrecipitated dicyclohexyl-urea is filtered off
  3. concentrationthe filtrate concentrated under vacuum
  4. additiondiluted with methanol
  5. additionH2O is added until the product
  6. customprecipitates
  7. filtrationThe precipitate is filtered
  8. washwashed with MeOH/H2O (4:1)
  9. customdried

Sources & evidence

ORD record
ord-27760fc0223a406b9b559019cc1ffa57
Source dataset
uspto-grants-1984_03
Patent number
US04435385

Reaction notes

Loading…