Dicyclohexylcarbodiimide → BOC-Phe-(D)Trp-Lys(Z)-OMe

HRID 1903340Notes

Reaction equation

HRID 1903340 reaction equation
C1C=CC2N(O)N=NC=2C=1.[NH:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:30][C@@H:31]([C:42]([NH:44][C@H:45]([C:61]([O:63][CH3:64])=[O:62])[CH2:46][CH2:47][CH2:48][CH2:49][NH:50][C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])=[O:43])[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH:34]=1.Cl.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CCN(CC)CC>[NH:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:12]([C:20]([NH:30][C@@H:31]([C:42]([NH:44][C@H:45]([C:61]([O:63][CH3:64])=[O:62])[CH2:46][CH2:47][CH2:48][CH2:49][NH:50][C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])=[O:43])[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH:34]=1)=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 13391306H-(D)Trp-Lys(Z)-OMe hydrochloride

Product 1

HCID 13391308BOC-Phe-(D)Trp-Lys(Z)-OMe

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-20 °C

Procedure

9.5 ml NEt3, 13 g HOBT and 17 g BOC-Phe-OH are added to 35 g H-(D)Trp-Lys(Z)-OMe hydrochloride in 350 ml DMF. The solution is cooled to -20° C. and 14.5 g DCCI dissolved in 50 ml DMF are added. The reaction mixture is stirred for ca. 18 hrs. at 0° C. and then for 1 day at room temperature. The precipitated dicyclohexyl-urea is filtered off and the filtrate is concentrated, diluted with methanol and H2O added until precipitation occurs. After filtration the residue is washed with MeOH/H2O (4:1) and dried to yield the title compound:

Workup

  1. additionare added
  2. waitat 0° C. and then for 1 day at room temperature
  3. filtrationThe precipitated dicyclohexyl-urea is filtered off
  4. concentrationthe filtrate is concentrated
  5. additiondiluted with methanol and H2O
  6. additionadded until precipitation
  7. filtrationAfter filtration the residue
  8. washis washed with MeOH/H2O (4:1)
  9. customdried

Sources & evidence

ORD record
ord-b6b161e30d1a491bb9b5bd50b1085533
Source dataset
uspto-grants-1984_03
Patent number
US04435385

Reaction notes

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