Diisopropylethylamine → 1,1-dimethylethyl (2-{[(4-bromo-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-phenylpropyl)carbamate

HRID 1845410노트

반응식

HRID 1845410 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=O)[N:5]([CH3:7])[CH:6]=1.[NH2:11][CH:12]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:11][CH:12]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:10])[N:5]([CH3:7])[CH:6]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 88932594-bromo-1-methyl-1H-pyrrole-2-carboxylic acidHCID 20159911tert-butyl N-(2-amino-3-phenylpropyl)carbamate

생성물 1

HCID 578267931,1-dimethylethyl (2-{[(4-bromo-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-phenylpropyl)carbamate수율 26%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a 50 mL round-bottomed flask was added 4-bromo-1-methyl-1H-pyrrole-2-carboxylic acid (610 mg, 3.0 mmol), 1,1-dimethylethyl (2-amino-3-phenylpropyl)carbamate (748 mg, 2.99 mmol) [prepared according to the procedure of Preparation 2] and PyBrop (1.71 g, 3.67 mmol) in Chloroform (15 mL). DIEA (1.8 mL, 10.3 mmol) was added and the mixture stirred overnight at room temperature. The reaction mixture was adsorbed onto silica and purified via column chromatography (Hex/EtOAc) affording the title compound (335 mg, 26%): LC-MS (ES) m/z=438 (M+H)+.

후처리

  1. customprepared
  2. custompurified via column chromatography (Hex/EtOAc)

출처 및 근거

ORD 기록
ord-193a3d6d610f4e99996b08a27c9c39ce
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946278B2

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