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Dicyclohexylcarbodiimide → alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide

HRID 1110467
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반응식

HRID 1110467 반응식
[CH3:1][C@H:2]([NH2:12])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[C:13](O)(=[O:22])[C@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:15].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>ClCCl.CO.CN(C)C=O>[OH:15][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([NH:12][CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:22]
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참가 물질

8

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 439616(S)-mandelic acidHCID 13739742(S)-2-Amino-5-(3-pyridyl)pentane

생성물 1

HCID 13999762alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide

시약·촉매·용매 3

HCID 887Methanol
용매
HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매

실험 절차

Under the conditions outlined in Example 14a, 76.2 g of the amine was reacted with 74.2 g of (S)-mandelic acid in the presence of 105.2 g of 1,3-dicyclohexylcarbodiimide and 78.4 g of 1-hydroxybenzotriazole in 1L of dimethylformamide. A similar workup furnished 109 g of [S-(S*,S*)]-alpha-hydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide, mp 143°-145° C., [α]D25 +27.8° (c, 1.0, MeOH).

출처 및 근거

ORD 기록
ord-913fb522c36f41f1b49859dbaa9e09ae
출처 데이터셋
uspto-grants-1990_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04975438

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