1-Hydroxybenzotriazole → N-[(S)-2-phenylpropionyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

HRID 1060399Notes

Reaction equation

HRID 1060399 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:22])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[CH:10][CH:9]=1)[NH2:6].[C:23]1([C@H:29]([CH3:33])[C:30](O)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH3:2][O:3][C:4](=[O:22])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[CH:10][CH:9]=1)[NH:6][C:30](=[O:31])[C@H:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:33]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27246222-Phenylpropionic acid, (+)-HCID 69377539HCID 69377539, compound

Product 1

HCID 53979202N-[(S)-2-phenylpropionyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl esterYield 79.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-methoxyphenyl)-L-phenylalanine methyl ester hydrochloride (0.03 g), (S)-2-phenylpropionic acid (0.014 g), EDC (0.02 g), HOBT (0.021 g) and DIEA (0.034 mL) in DMF (5 mL) was stirred at room temperature for 18 h. DMF was removed and the residue was partitioned between EtOAc and water. The organic layer was evaporated and washed sequentially with 10% citric acid, satd. NaHCO3 and brine. The resulting organic layer was dried (MgSO4), evaporated and the residue was purified by flash column chromatography (silica gel; eluent: CH2Cl2/EtOAc 9:1) to yield N-[(S)-2-phenylpropionyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (0.031 g). ESMS: m/z 417 (MH+).

Workup

  1. customDMF was removed
  2. customthe residue was partitioned between EtOAc and water
  3. customThe organic layer was evaporated
  4. washwashed sequentially with 10% citric acid
  5. dry with materialThe resulting organic layer was dried (MgSO4)
  6. customevaporated
  7. customthe residue was purified by flash column chromatography (silica gel; eluent: CH2Cl2/EtOAc 9:1)

Sources & evidence

ORD record
ord-26b454e6d8604e48a67dd030156e1e7a
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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