Methoxyacetic Acid → HCID 16727991, compound

HRID 1596323Notes

Reaction equation

HRID 1596323 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:29][C:30]1[CH:66]=[CH:65][CH:64]=[CH:63][C:31]=1[CH2:32][NH:33][C:34]([C@@H:36]1[C:40]([CH3:42])([CH3:41])[S:39][CH2:38][N:37]1[C:43](=[O:62])[C@@H:44]([OH:61])[C@@H:45]([NH:53][C:54](=[O:60])[C@H:55]([CH:57]([CH3:59])[CH3:58])[NH2:56])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:35]>CN(C=O)C.C(OCC)(=O)C>[CH3:29][C:30]1[CH:66]=[CH:65][CH:64]=[CH:63][C:31]=1[CH2:32][NH:33][C:34]([C@@H:36]1[C:40]([CH3:42])([CH3:41])[S:39][CH2:38][N:37]1[C:43](=[O:62])[C@@H:44]([OH:61])[C@@H:45]([NH:53][C:54](=[O:60])[C@@H:55]([NH:56][C:4](=[O:6])[CH2:3][O:2][CH3:1])[CH:57]([CH3:59])[CH3:58])[CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)=[O:35]

Participants

7

Reactant 4

HCID 12251Methoxyacetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20686737HCID 20686737, compound

Product 1

HCID 16727991HCID 16727991, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methoxyacetic acid (23 μl), HOBt (48 mg), and EDC.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 (149 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-9e4f2d8df82a4d7593c9127835415ea1
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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