Acetic Acid → 1-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate

HRID 2233944노트

반응식

HRID 2233944 반응식
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7](O)[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].Cl.[Cl:19][C:20]1[C:24]([Cl:25])=[C:23]([CH3:26])[NH:22][C:21]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.CCOCC>[Cl:19][C:20]1[C:24]([Cl:25])=[C:23]([CH3:26])[NH:22][C:21]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][N:33]([CH:7]2[CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:4]([C:3]([O:2][CH3:1])=[O:17])[CH2:8]2)[CH2:32][CH2:31]1)=[O:28]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 68579996HCID 68579996, 화합물2회

생성물 1

HCID 866082951-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 3283Diethyl Ether용매

실험 절차

N-BOC-trans-4-Hydroxy-L-proline methylester (0.20 g, 0.81 mM) and 3,4-dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide (free base of Intermediate 1), 0.16 g, 0.81 mM) were stirred in 1,2-dichloroethane (3.5 ml). Sodium triacetoxyborohydride (0.24 g, 1.1 mM) was added followed by acetic acid (0.05 ml). The reaction was stirred under nitrogen at room temperature overnight then diluted with ether and washed with 1 N sodium hydroxide. The organic phase was washed with brine, dried over MgSO4 and concentrated to give an orange oil. The oil was chromatographed using EtOAc to give the desired product as a light yellow solid.

후처리

  1. washwashed with 1 N sodium hydroxide
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give an orange oil
  6. customThe oil was chromatographed

출처 및 근거

ORD 기록
ord-3f684d12d6864294a450c20e06ae6240
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709503B2

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