Methanol → HCID 68616941, compound

HRID 1158376Notes

Reaction equation

HRID 1158376 reaction equation
C(OC([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]([CH:34]=O)[CH2:9]1)=O)(C)(C)C.[CH2:36]([NH2:38])[CH3:37].CO.[BH4-].[Na+]>O.CC#N.CC#N.O.C(Cl)Cl.CO>[CH2:36]([NH:38][CH2:34][C@@H:10]1[CH2:9][NH:8][CH2:12][C@H:11]1[CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]1[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]=1)[CH3:37]

Participants

9

Reactant 4

HCID 887MethanolHCID 6341EthylamineHCID 4311764Sodium borohydrideHCID 59512275(3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68616941HCID 68616941, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 18373917Acetonitrile--water (1/1)SolventHCID 21226129Dichloromethane methanolSolvent2×

Procedure

The title compound is prepared from (3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.75 g, 1.52 mmol), 2N solution of ethylamine in MeOH (3.805 mL, 7.61 mmol) and NaBH4 (0.115 g, 3.04 mmol) and purification by flash chromatography on silica gel (CH2Cl2/MeOH 96:4, then CH2Cl2/MeOH (10% NH3 conc.) gradient from 9:1 to 8:2) to give a colorless oil. MS: 522.4 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 4.47 min.

Workup

  1. custom4.47 min.

Sources & evidence

ORD record
ord-78d876aa825041ada4abedfb196243d5
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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