Dicyclohexylcarbodiimide → HCID 178427504, compound

HRID 1417889Notes

Reaction equation

HRID 1417889 reaction equation
[NH:1]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@@H:2]([C:14]([N:16]([CH3:42])[C@H:17]([C:35]([NH:37][CH2:38][C:39]([OH:41])=[O:40])=[O:36])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:34])[NH:23][S:24]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].O[N:51]1[C:56](=[O:57])[CH2:55][CH2:54][C:52]1=[O:53].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@@H:2]([C:14]([N:16]([CH3:42])[C@H:17]([C:35]([NH:37][CH2:38][C:39]([O:41][N:51]1[C:56](=[O:57])[CH2:55][CH2:54][C:52]1=[O:53])=[O:40])=[O:36])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:34])[NH:23][S:24]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:25])=[O:26])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([C:10]([F:11])([F:13])[F:12])=[O:9]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 178427505HCID 178427505, compound

Product 1

HCID 178427504HCID 178427504, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-D-Lys(Tfa)-NMeArg(Tos)-Gly (8.00 g, 11.0 mmol), HOSu (1.25 g, 10.8 mmol) and DCC (2.22 g, 10.8 mmol) were dissolved in DMF (75 ml) and stirred at room temperature for 2 days. The solids were removed by filtration and washed with DMF (2×15 ml). The filtrate was concentrated under reduced pressure and the resulting syrup dried under reduced pressure at 40° C. to give a tan solid (6.50 g, 72%). MP=66°-69° C.; FAB-MS: [M+H]=821.

Workup

  1. customThe solids were removed by filtration
  2. washwashed with DMF (2×15 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting syrup dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-f991f628861d4a629825b21ab28c4227
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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