HCID 131723025, compound → HCID 59977253, compound

HRID 393055Notes

Reaction equation

HRID 393055 reaction equation
[CH3:1][C:2]1[CH:24]=[C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[O:26])[CH:22]=[C:21]([CH3:36])[C:3]=1[C:4]([NH:6][C@H:7]([C:17]([O:19][CH3:20])=[O:18])[CH2:8][NH:9]C(OC(C)(C)C)=O)=[O:5]>FC(F)(F)C(O)=O.ClCCl>[NH2:9][CH2:8][C@@H:7]([C:17]([O:19][CH3:20])=[O:18])[NH:6][C:4](=[O:5])[C:3]1[C:2]([CH3:1])=[CH:24][C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[O:26])=[CH:22][C:21]=1[CH3:36]

Participants

4

Reactant 1

HCID 131723025HCID 131723025, compound

Product 1

HCID 59977253HCID 59977253, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of crude N-[2,6-dimethyl-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine, methyl ester (144 mg, 0.235 mmol) in trifluoroacetic acid (2 mL) and dichloromethane (2 mL) was stirred at room temperature for 1 h. The reaction mixture was concentrated and ethyl acetate was added. The solution was washed with saturated aqueous sodium hydrogen carbonate, and the aqueous layer was back-extracted seven times with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and evaporated to give crude 3-amino-N-[2,6-dimethyl-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester (104 mg, 110% of the theoretical amount).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate was added
  3. washThe solution was washed with saturated aqueous sodium hydrogen carbonate
  4. extractionthe aqueous layer was back-extracted seven times with ethyl acetate
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-87118de2a1ab43d190fa3526fa9c0b35
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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