Tetrahydrofuran → 3-(4-Benzyloxy-phenyl)-2-[4-methyl-2-(tetrahydro-pyran-4-ylamino)-pentanoylamino]-propionic acid tert-butyl ester

HRID 1953916Notes

Reaction equation

HRID 1953916 reaction equation
[C:1]([O:5][C:6](=[O:46])[CH:7]([NH:23][C:24](=[O:45])[CH:25]([NH:30]CC1C2C=CC=CC=2C2C1=CC=CC=2)[CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].N1[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1.[O:53]1CCCC1>>[C:1]([O:5][C:6](=[O:46])[CH:7]([NH:23][C:24](=[O:45])[CH:25]([NH:30][CH:50]1[CH2:51][CH2:52][O:53][CH2:48][CH2:49]1)[CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8082PiperidineHCID 545401193-(4-Benzyloxy-phenyl)-2-{2-[(9H-fluoren-9-ylmethyl)-amino]-4-methyl-pentanoylamino}-propionic acid tert-butyl ester

Product 1

HCID 700696313-(4-Benzyloxy-phenyl)-2-[4-methyl-2-(tetrahydro-pyran-4-ylamino)-pentanoylamino]-propionic acid tert-butyl esterYield 77%

Procedure

A solution of [S-(R*,R*)]-3-(4-benzyloxy-phenyl)-2-{2-[(9H-fluoren-9-ylmethyl)-amino]-4-methyl pentanoylamino}-propionic acid tert-butyl ester (12.2 g, 20.0 mmol) in 500 mL of tetrahydrofuran was treated with piperidine (80 mL). The resulting solution was stirred at room temperature for 48 hours. The reaction mixture was concentrated and the residue purified by chromatography (SiO2, gradient elution EtOAc - 15% EtOH/EtOAc). The resulting yellow solid was broken up in heptane to give the title compound as a white solid (6.77 g, 77%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by chromatography (SiO2, gradient elution EtOAc - 15% EtOH/EtOAc)

Sources & evidence

ORD record
ord-953c97ed942f4ab1a0dae2f86c447492
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

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