(R)-1-(Pyridin-3-yl)ethanamine → tert-butyl-(3R)-3-({[(1S)-2,2-dimethyl-1-{[(1R)-1-(3-pyridyl)ethylamino]carbonyl}propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]-hexanoate

HRID 1701011Notes

Reaction equation

HRID 1701011 reaction equation
[C:1]([C@@H:4]([NH:9][C:10]([C@H:12]([CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:26]([CH3:36])[CH:25]=1)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:11])[C:5]([CH3:8])([CH3:7])[CH3:6])(O)=[O:2].[N:37]1[CH:42]=[CH:41][CH:40]=[C:39]([C@H:43]([NH2:45])[CH3:44])[CH:38]=1>>[C:17]([O:16][C:14](=[O:15])[CH2:13][C@H:12]([C:10]([NH:9][C@H:4]([C:1]([NH:45][C@@H:43]([C:39]1[CH:38]=[N:37][CH:42]=[CH:41][CH:40]=1)[CH3:44])=[O:2])[C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11])[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[C:26]([CH3:36])[CH:25]=1)([CH3:18])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 1084920(R)-1-(Pyridin-3-yl)ethanamineHCID 59875725tert-butyl (3R)-3-({[(1S)-1-(carboxy)-2,2-dimethylpropyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hexanoate

Product 1

HCID 54327310tert-butyl-(3R)-3-({[(1S)-2,2-dimethyl-1-{[(1R)-1-(3-pyridyl)ethylamino]carbonyl}propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]-hexanoateYield 89.5%

Procedure

According to the method of Example 25(a), tert-butyl (3R)-3-({[(1S)-1-(carboxy)-2,2-dimethylpropyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hexanoate (Preparation 19c)(497 mg, 1.0 mmol) was reacted with (R)-(+)-1-(3-pyridyl)ethylamine (122 mg, 1.0 mmol) at room temperature for 2.5 h, followed by the same work up and purification by flash chromatography (gradient elution with hexane:ethyl acetate 4:1 to 100% ethyl acetate) gave tert-butyl-(3R)-3-({[(1S)-2,2-dimethyl-1-{[(1R)-1-(3-pyridyl)ethylamino]carbonyl}propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]-hexanoate (537 mg, 89%) as a colourless foam.

Workup

  1. custompurification
  2. washby flash chromatography (gradient elution with hexane:ethyl acetate 4:1 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-6d48fdb5e1dc42d8ba4bd84fe776d311
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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