Hydrochloric Acid → (S)-3-((S)-1-Cyclopentyloxycarbonyl-3-methyl-butylcarbamoyl)-7-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 2360648노트

반응식

HRID 2360648 반응식
[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18](O)=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:21]([O-:23])=[O:22])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[CH:34]1([O:39][C:40](=[O:47])[C@H:41]([CH2:43][CH:44]([CH3:46])[CH3:45])[NH2:42])[CH2:38][CH2:37][CH2:36][CH2:35]1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl.Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18](=[O:19])[NH:42][C@H:41]([C:40]([O:39][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38]2)=[O:47])[CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:21]([O-:23])=[O:22])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoateHCID 67052655(S)-2-(tert-butoxycarbonyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

생성물 1

HCID 57971746(S)-3-((S)-1-Cyclopentyloxycarbonyl-3-methyl-butylcarbamoyl)-7-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(S)-7-Nitro-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid-2-tert-butyl ester (2.5 g, 7.76 mmol) was dissolved in DCM (100 ml). HOBt (1.16 g, 8.53 mmol) was added, L-leucine cyclopentyl ester (3.19 g, 8.53 mmol) was added followed by triethylamine (2.38 ml, 17.1 mmol). EDCl.HCl (1.46 g, 8.5 mmol) was added and the reaction stirred at room temperature for 16 h. To the reaction was added DCM (100 ml) and the organic layer washed with water (3×300 ml), dried with Na2SO4 and the solvent removed in vacuo. The crude product was purified by chromatography (EtOAc:heptane 1:2→EtOAc) to give the required product 3.14 g (82% yield), LCMS purity 100%, m/z 504 [M++H]+

후처리

  1. washthe organic layer washed with water (3×300 ml)
  2. dry with materialdried with Na2SO4
  3. customthe solvent removed in vacuo
  4. customThe crude product was purified by chromatography (EtOAc:heptane 1:2→EtOAc)

출처 및 근거

ORD 기록
ord-08b16f1ff09441d0b057194bf47256c2
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08686032B2

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