Hydrochloric Acid → HCID 16727992, compound

HRID 1596324Notes

Reaction equation

HRID 1596324 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([OH:7])=O)[CH3:2].C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:19][C:20]1[CH:56]=[CH:55][CH:54]=[CH:53][C:21]=1[CH2:22][NH:23][C:24]([C@@H:26]1[C:30]([CH3:32])([CH3:31])[S:29][CH2:28][N:27]1[C:33](=[O:52])[C@@H:34]([OH:51])[C@@H:35]([NH:43][C:44](=[O:50])[C@H:45]([CH:47]([CH3:49])[CH3:48])[NH2:46])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:25]>CN(C=O)C.C(OCC)(=O)C>[CH3:19][C:20]1[CH:56]=[CH:55][CH:54]=[CH:53][C:21]=1[CH2:22][NH:23][C:24]([C@@H:26]1[C:30]([CH3:32])([CH3:31])[S:29][CH2:28][N:27]1[C:33](=[O:52])[C@@H:34]([OH:51])[C@@H:35]([NH:43][C:44](=[O:50])[C@@H:45]([NH:46][C:5](=[O:7])[CH2:4][O:3][CH2:1][CH3:2])[CH:47]([CH3:49])[CH3:48])[CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12301Ethoxyacetic acidHCID 757711-HydroxybenzotriazoleHCID 20686737HCID 20686737, compound

Product 1

HCID 16727992HCID 16727992, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethoxyacetic acid (28 μl), HOBt (41 mg), and HDC.HCl (63 mg) were added to a solution of H-Val-Apns-Dmt-NHBzl(2-Me) (162 mg) obtained in the step 2 of Example 8 in DMF (5 ml) and the mixture was stirred overnight. After the addition of ethyl acetate, the reaction mixture was washed with 3% Na2CO3, 1N HCl, and 5% NaCl and dried over MgSO4. After filtration and concentration, the residue was recrystallized from ethyl acetate/n-hexane to obtain the title compound (153 mg).

Workup

  1. washthe reaction mixture was washed with 3% Na2CO3, 1N HCl, and 5% NaCl
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-fd8689badb684a59b2d37324d4724bc8
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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