1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl (2S,3R)-3-hydroxy-1-phenyl-4-(5-(prop-1-en-2-yl)nicotinamido)butan-2-ylcarbamate

HRID 2071185노트

반응식

HRID 2071185 반응식
[CH2:1]=[C:2]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=O)[CH3:3].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:34][CH2:35][C@@H:36]([OH:53])[C@@H:37]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CCN(C(C)C)C(C)C>ClCCl>[OH:53][C@H:36]([CH2:35][NH:34][C:9](=[O:11])[C:8]1[CH:12]=[C:4]([C:2]([CH3:3])=[CH2:1])[CH:5]=[N:6][CH:7]=1)[C@@H:37]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:49])[CH3:50])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10333883tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamateHCID 686704595-(Prop-1-en-2-yl)nicotinic acid

생성물 1

HCID 86647444tert-butyl (2S,3R)-3-hydroxy-1-phenyl-4-(5-(prop-1-en-2-yl)nicotinamido)butan-2-ylcarbamate수율 53.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 5-(prop-1-en-2-yl)nicotinic acid (200 mg, 1.23 mmol) in dichlormethane (10 ml) at rt, EDCI (330 mg, 1.72 mmol) and HOBT (200 mg, 1.48 mmol) were added. After stirring at rt for 10 minutes, tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate (344 mg, 1.23 mmol) was added followed by DIPEA (0.2 ml). After stirring overnight at rt, reaction mixture was worked up as usual and residue was column purified (90% ethylacetate/10% hexanes) to yield 280 mg of tert-butyl (2S,3R)-3-hydroxy-1-phenyl-4-(5-(prop-1-en-2-yl)nicotinamido)butan-2-ylcarbamate, which on stirring with 4N HCl in dioxane for 4 h yields the HCl salt of N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-5-(prop-1-en-2-yl)nicotinamide.

후처리

  1. stirringAfter stirring overnight at rt
  2. customreaction mixture
  3. custompurified (90% ethylacetate/10% hexanes)

출처 및 근거

ORD 기록
ord-18eb0325680e4480bfc472267b5c7856
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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