Triethylamine → HCID 16727990, compound

HRID 1596322Notes

Reaction equation

HRID 1596322 reaction equation
[C:1](=O)([O:7]C1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][CH2:4][O:5][CH3:6].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:35][C:36]1[CH:72]=[CH:71][CH:70]=[CH:69][C:37]=1[CH2:38][NH:39][C:40]([C@@H:42]1[C:46]([CH3:48])([CH3:47])[S:45][CH2:44][N:43]1[C:49](=[O:68])[C@@H:50]([OH:67])[C@@H:51]([NH:59][C:60](=[O:66])[C@H:61]([CH:63]([CH3:65])[CH3:64])[NH2:62])[CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:41]>CN(C=O)C.C(OCC)(=O)C>[CH3:35][C:36]1[CH:72]=[CH:71][CH:70]=[CH:69][C:37]=1[CH2:38][NH:39][C:40]([C@@H:42]1[C:46]([CH3:48])([CH3:47])[S:45][CH2:44][N:43]1[C:49](=[O:68])[C@@H:50]([OH:67])[C@@H:51]([NH:59][C:60](=[O:66])[C@@H:61]([NH:62][C:1]([O:2][CH2:3][CH2:4][O:5][CH3:6])=[O:7])[CH:63]([CH3:65])[CH3:64])[CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)=[O:41]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 20686737HCID 20686737, compoundHCID 219482932-Methoxyethyl 4-nitrophenyl carbonate

Product 1

HCID 16727990HCID 16727990, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methoxyethyl p-nitrophenyl carbonate (112 mg), HOBt (41 mg), triethylamine (104 μl) were added to a solution of H-Val-Apns-Dmt-NHBzl(2-Me) 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 purified using silica gel column chromatography and reprecipitated from ethyl acetate/n-hexane to obtain the title compound (130 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 purified
  5. customreprecipitated from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-22243f974a104c70a6972b6b9ad76b05
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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