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Methylamine → ethyl (2S,3S)-3-amino-2-hydroxy-4-phenylbutyrate

HRID 1721712
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HRID 1721712 반응식
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:13]([OH:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].CN.C(Cl)Cl.CO>C(O)C>[NH2:3][C@@H:12]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C@H:13]([OH:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]
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참가 물질

5

반응물 3

HCID 6329MethylamineHCID 21226129Dichloromethane methanolHCID 54031650Ethyl 3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-hydroxy-4-phenylbutyrate

생성물 1

HCID 54193969ethyl (2S,3S)-3-amino-2-hydroxy-4-phenylbutyrate수율 82%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

Analogously to Example 23, by reacting a solution of 10.42 g of a 95:5 mixture of the (2S,3S) and (2R,3S) isomers of ethyl 3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-hydroxy-4-phenylbutyrate (Example 20) in 10 ml of ethanol with 5.9 ml of a 33% solution of methylamine in ethanol there are obtained 5.39 g (82%) of ethyl (2S,3S)-3-amino-2-hydroxy-4-phenylbutyrate, TLC (SiO2, CH2Cl2 /methanol 10:1, UV254): Rf =0.34.

출처 및 근거

ORD 기록
ord-232affe0139a4acab95ddc0e11c398fc
출처 데이터셋
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05512682

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