tert-Butyl Formate → (3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158357

반응식

HRID 1158357 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][OH:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OC(C)(C)C)=O.CC#N.O>C(Cl)Cl.O.CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:32])[CH3:33])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH:34]=[O:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 61207tert-Butyl FormateHCID 159087TriacetoxyperiodinaneHCID 18373917Acetonitrile--water (1/1)HCID 59512299(3S,4R)-3-Hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 59512275(3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매2회HCID 6344Dichloromethane용매2회

실험 절차

The title compound is prepared in a similar manner as described for Example 9/reaction step I, from (3S*,4R*)-3-hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (4.9 g, 9.95 mmol) and Dess-Martin periodinane (4.22 g, 9.95 mmol) in CH2Cl2 (30 mL), slowly wet CH2Cl2 (0.20 mL of water in 30 mL of CH2Cl2) as colorless oil. MS: 437.2 [M+H-BOC]+. tR (HPLC, Nucleosil C18 column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/1.5 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 4.99 min.

후처리

  1. custom4.99 min.

출처 및 근거

ORD 기록
ord-5dad337c3a9f49ceb883707d9e914e2d
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807709B2

연결된 노트

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