Methanol → 2-tert-Butoxycarbonylamino-3-(3-aminopyridin-2-ylamino)propionic acid methyl ester

HRID 2230473Notes

Reaction equation

HRID 2230473 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][NH:14][C:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.Cl.[CH3:25]N(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH3:25][O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][NH:14][C:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184658332-tert-Butoxycarbonylamino-3-(3-aminopyridin-2-ylamino)-propionic acid

Product 1

HCID 545176622-tert-Butoxycarbonylamino-3-(3-aminopyridin-2-ylamino)propionic acid methyl esterYield 67%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S) 2-tert-Butoxycarbonylamino-3-(3-aminopyridin-2-ylamino)-propionic acid (360 mg, 1.21 mmol) and MeOH (59 mg, 1.82 mmol) in anhydrous CH2Cl2 (20 ml) was treated with 4-dimethylaminopyridine (DMAP, 163 mg, 1.33 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (280 mg, 1.45 mmol). The reaction was stirred for 18 h, diluted with EtOAc (150 ml), washed with water (2×), sat. aq. NaHCO3, and sat. aq. NaCl, dried over Na2SO4 and concentrated in vacuo. Chromatography (flash, SiO2, 0 to 5% MeOH/CH2Cl2) gave 250 mg (67%) of the title compound as a light tan solid.

Workup

  1. washwashed with water (2×), sat. aq. NaHCO3, and sat. aq. NaCl
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea84c5bceb3e4318bcfae65b4d5fcaef
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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