Dicyclohexylcarbodiimide → HCID 13996501, compound

HRID 1638572Notes

Reaction equation

HRID 1638572 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:29]([O:31][CH3:32])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])[C@H:14]([CH2:16][CH3:17])[CH3:15])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([N:50]2[CH:54]=[N:53][C:52]([CH2:55][C@H:56]([NH:60]C(OC(C)(C)C)=O)[C:57]([OH:59])=O)=[CH:51]2)(=[O:49])=[O:48])=[CH:43][CH:42]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(O)(C(F)(F)F)=O.C(Cl)Cl.CC(O)=O>[NH2:60][C@H:56]([C:57]([NH:1][C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:29]([O:31][CH3:32])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])[C@H:14]([CH2:16][CH3:17])[CH3:15])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:5])[CH3:6])=[O:59])[CH2:55][C:52]1[N:53]=[CH:54][N:50]([S:47]([C:44]2[CH:43]=[CH:42][C:41]([CH3:40])=[CH:46][CH:45]=2)(=[O:48])=[O:49])[CH:51]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 6455010Boc-His(Tos)-OHHCID 13996441HCID 13996441, compound

Product 1

HCID 13996501HCID 13996501, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Stir 0.40 g (0728 mmoles) of Boc-Sta-Ile-Phe-OCH3, as prepared in Preparation XX10II above, in 6 ml of TFA-CH2Cl2 (1:1 v/v) at room temperature for 30 minutes. Remove the solvent in vacuo and extract the residue with CH2Cl2 and aq. NaHCO3. Filter the organic layers through Na2SO4 into a flask containing 0.42 g (1.02 mmoles) of Boc-His-(Tos), concentrate the solution to a volume of about 25 ml, and add 0.21 g (1.02 mmoles) of DCC. Stir for 40 minutes, then add 1 drop of HOAc and filter off DCU. Extract the filtrate with aq. NaHCO3, filter the organic layers through Na2SO4, and remove the solvent in vacuo. The crude product is applied to a silica gel chromatography column and the product is eluted with 4% MeOH-96% CH2Cl2 to give 0.566 g (93%) of Box-His(Tos)-Sta-Ile-Phe-OCH3.

Workup

  1. customRemove the solvent in vacuo
  2. extractionextract the residue with CH2Cl2 and aq. NaHCO3
  3. filtrationFilter the organic layers through Na2SO4 into a flask
  4. concentrationconcentrate the solution to a volume of about 25 ml
  5. filtrationfilter off DCU
  6. extractionExtract the filtrate with aq. NaHCO3
  7. filtrationfilter the organic layers through Na2SO4
  8. customremove the solvent in vacuo
  9. washthe product is eluted with 4% MeOH-96% CH2Cl2

Sources & evidence

ORD record
ord-ec5eb90055ee4c30b25f72888c68a905
Source dataset
uspto-grants-1989_11
Patent number
US04880781

Reaction notes

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