Dicyclohexylcarbodiimide → HCID 86715380, compound

HRID 628168Notes

Reaction equation

HRID 628168 reaction equation
O[C@@:2]([CH3:54])([C:5](=[O:53])[C@@H:6]([NH:11][C:12](=[O:52])[C@@H:13]([NH:21][C:22](=[O:51])[C@@H:23]([N:28](C)[C:29](=[O:49])[C@@H:30]([NH:39][C:40](=[O:48])[CH2:41][N:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1)[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:3][I:4].[CH3:55][O:56][C:57]1[CH:71]=[CH:70][C:60]([CH2:61][O:62][C:63](=[O:69])[CH2:64][CH2:65][C:66]([OH:68])=[O:67])=[CH:59][CH:58]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:66]([O:68][C@:2]([CH3:54])([CH2:3][I:4])[C:5](=[O:53])[C@H:6]([CH2:7][CH:8]([CH3:9])[CH3:10])[NH:11][C:12](=[O:52])[C@H:13]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:21][C:22](=[O:51])[C@H:23]([CH2:24][CH:25]([CH3:27])[CH3:26])[NH:28][C:29](=[O:49])[C@H:30]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[NH:39][C:40](=[O:48])[CH2:41][N:42]1[CH2:43][CH2:44][O:45][CH2:46][CH2:47]1)(=[O:67])[CH2:65][CH2:64][C:63]([O:62][CH2:61][C:60]1[CH:59]=[CH:58][C:57]([O:56][CH3:55])=[CH:71][CH:70]=1)=[O:69]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11042776HCID 11042776, compoundHCID 86715381HCID 86715381, compound

Product 1

HCID 86715380HCID 86715380, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
30 °C

Procedure

Referring to FIG. 43, to a solution of compound (S)—N—((S)-1-(((2S,4S)-2-hydroxy-1-iodo-2,6-dimethyl-3-oxoheptan-4-yl)amino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)—N-methyl-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide (20, 1.5 g, 1.77 mmol) in DCM (10 mL) were added 4-((4-methoxybenzyl)oxy)-4-oxobutanoic acid (2.1 g, 8.81 mmol), DCC (1.82 g, 8.82 mmol) and DMAP (1.08 g, 8.84 mmol). The reaction mixture was stirred for 3 h at 30° C. (TLC analysis showed very little of 19 was left). The mixture was diluted with DCM (100 mL) and then filtered. The filtrate was washed with saturated citric acid solution (50 mL×2) and saturated NaHCO3 solution (50 mL×3), dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash column chromatography (EtOAc/DCM=1:15 to 2:1) to give product (1.7 g, 90% yield) as a yellow powder.

Workup

  1. waitwas left)
  2. filtrationfiltered
  3. washThe filtrate was washed with saturated citric acid solution (50 mL×2) and saturated NaHCO3 solution (50 mL×3)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (EtOAc/DCM=1:15 to 2:1)

Sources & evidence

ORD record
ord-c1b6cbf1d9e74272b12711f96d32f2ea
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

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