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

HRID 24626
노트
인쇄 미리보기

반응식

HRID 24626 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 11
1,2-Dichloroethane
용매
HCID 6228Dimethylformamide용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-7d51d67125a74d61b9dadd0cb93743d1
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06855843B2

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