Dimethylamine → HCID 58402898, compound

HRID 2093309Notes

Reaction equation

HRID 2093309 reaction equation
C1C2C(COC(=O)[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([NH:45][C:46](=[O:58])[C@@H:47]([N:49]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH3:50])[CH3:48])[C:23]([N:25]3[CH2:29][CH2:28][CH2:27][C@H:26]3[C:30]3[CH:31]=[N:32][CH:33]=[C:34]([C:36](=[O:44])[C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[CH:35]=3)=[O:24])C3C(=CC=CC=3)C=2C=CC=1.CNC>C1COCC1>[C:54]([O:53][C:51](=[O:52])[N:49]([C@H:47]([C:46](=[O:58])[NH:45][C@H:22]([C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[C:30]1[CH:31]=[N:32][CH:33]=[C:34]([C:36](=[O:44])[C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)[CH:35]=1)=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][NH2:17])[CH3:48])[CH3:50])([CH3:55])([CH3:56])[CH3:57]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 67339407HCID 67339407, compound

Product 1

HCID 58402898HCID 58402898, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ((S)-5-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-6-{(S)-2-[5-(4-fluoro-benzoyl)-pyridin-3-yl]-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (I-1c: 2.98 g, 3.7 mmol) was added 2M dimethylamine in THF (20 mL) and the mixture was stirred for 2 hours. The reaction mixture was concentrated in vacuo and purification was accomplished with semi-preparative reverse phase HPLC (300×50 mm) eluting w/10-60% acetonitrile/water over 45 minutes, followed by lyophilization of the desired fractions to provide [(S)-1-((S)-5-amino-1-{(S)-2-[5-(4-fluoro-benzoyl)-pyridin-3-yl]-pyrrolidine-1-carbonyl}-pentylcarbamoyl)-ethyl]-methyl-carbamic acid tert-butyl ester (1.5 g, 69% over 4 steps).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and purification
  2. washeluting w/10-60% acetonitrile/water over 45 minutes

Sources & evidence

ORD record
ord-2f089cb9d98743ae8a0793b19ceb9c0e
Source dataset
uspto-grants-2013_05
Patent number
US08445440B2

Reaction notes

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