Dicyclohexylcarbodiimide → HCID 86715378, compound

HRID 630635Notes

Reaction equation

HRID 630635 reaction equation
[OH:1][C@@:2]([CH3:53])([C:5](=[O:52])[C@@H:6]([NH:11][C:12]([C@@H:14]([NH:22][C:23](=[O:51])[C@@H:24]([NH:29][C:30](=[O:50])[C@@H:31]([NH:40][C:41](=[O:49])[CH2:42][N:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1)[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:3][I:4].[C:54](O)(=[O:59])[CH2:55][CH2:56][C:57]#[CH:58].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:54]([O:1][C@:2]([CH3:53])([CH2:3][I:4])[C:5](=[O:52])[C@H:6]([CH2:7][CH:8]([CH3:9])[CH3:10])[NH:11][C:12](=[O:13])[C@H:14]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH:22][C:23](=[O:51])[C@H:24]([CH2:25][CH:26]([CH3:27])[CH3:28])[NH:29][C:30](=[O:50])[C@H:31]([CH2:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[NH:40][C:41](=[O:49])[CH2:42][N:43]1[CH2:44][CH2:45][O:46][CH2:47][CH2:48]1)(=[O:59])[CH2:55][CH2:56][C:57]#[CH:58]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 224644-Pentynoic acidHCID 86715379HCID 86715379, compound

Product 1

HCID 86715378HCID 86715378, compoundYield 41.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S)—N—((S)-1-((2S,4S)-2-hydroxy-1-iodo-2,6-dimethyl-3-oxoheptan-4-yl carbamoyl)-2-phenylethyl)-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)-4-methylpentanamide (1.18 g, 1.39 mmol) was dissolved in DMF. DMAP (19.2 mg, 0.139 mmol), 4-pentynoic acid (205 mg, 2.09 mmol) and DCC (430 mg, 2.09 mmol) were added. The mixture was stirred at room temperature for 16 hours and then diluted with 200 mL EtOAc. The organic phase was washed with 1N HCl (50 ml), brine (50 mL), and saturated NaHCO3 solution. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was purified by prep HPLC to afford 539 mg of product as a white solid.

Workup

  1. washThe organic phase was washed with 1N HCl (50 ml), brine (50 mL), and saturated NaHCO3 solution
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-f629280f552742ed98144bdccf73f3c5
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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