Dicyclohexylcarbodiimide → HCID 86746939, compound

HRID 1587603Notes

Reaction equation

HRID 1587603 reaction equation
CC(C)(OC(N[C@H](C(N[C@H](C([NH:26][C@@H:27]([CH2:38][CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)[CH:28]([P:30]([O:35][CH2:36][CH3:37])([O:32][CH2:33][CH3:34])=[O:31])[OH:29])=O)CC(C)C)=O)CC1C=CC=CC=1)=O)C.[CH3:46][C:47]([CH3:72])([O:49][C:50]([NH:52][C@H:53]([C:69](O)=[O:70])[CH2:54][C:55]1[N:59]([CH2:60][O:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:58]=[N:57][CH:56]=1)=[O:51])[CH3:48].O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:46][C:47]([CH3:48])([O:49][C:50]([NH:52][C@H:53]([C:69]([NH:26][C@@H:27]([CH2:38][CH:39]1[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1)[CH:28]([P:30]([O:35][CH2:36][CH3:37])([O:32][CH2:33][CH3:34])=[O:31])[OH:29])=[O:70])[CH2:54][C:55]1[N:59]([CH2:60][O:61][CH2:62][C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH:58]=[N:57][CH:56]=1)=[O:51])[CH3:72]

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 7023105HCID 7023105, compoundHCID 86746940HCID 86746940, compound

Product 1

HCID 86746939HCID 86746939, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound B from Example 2 (1.47 g, 4.46 mmol) was added to a solution of [(1,1-dimethylethoxy)carbonyl]-3-[(phenylmethoxy)methyl]-L-histidine (T. Brown and J. H. Jones, Journal of Chemical Society, Chemical Communications (1981), 648) in tetrahydrofuran (22 mL) and cooled to 0° C. 1-Hydroxybenzotriazole hydrate (682 mg, 4.46 mmol), N,N-diisopropylethylamine (854.5 μl, 4.9 mmol) and dicyclohexylcarbodiimide (920 mg, 4.46 mmol) were added sequentially. After 16 hours at 25° C., the reaction mixture was filtered and concentrated. The residue was dissolved in ethyl acetate (60 mL), washed sequentially with saturated aqueous sodium hydrogen carbonate (2×40 mL), saturated aqueous sodium chloride (40 mL), dried (Na2HSO4) and concentrated. Repeated purifications by column chromatography of the crude product (2.9 g) yielded 2.03 g (70.2%) of pure title A compound.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (60 mL)
  4. washwashed sequentially with saturated aqueous sodium hydrogen carbonate (2×40 mL), saturated aqueous sodium chloride (40 mL)
  5. dry with materialdried (Na2HSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-92e80a982cd7454ebd069f7cb1e1a797
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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