Diisopropylethylamine → HCID 71113060, compound

HRID 927847Notes

Reaction equation

HRID 927847 reaction equation
[CH:1]1([CH2:4][C@H:5]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:20][CH2:19]3)=[C:14]([O:21][CH2:22][CH:23]3[CH2:25][CH2:24]3)[N:13]=2)=[O:11])[C:6](O)=[O:7])[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:57][N:58]1[CH2:62][CH2:61][CH:60]([OH:63])[CH2:59]1>CN(C=O)C>[CH:1]1([CH2:4][C@H:5]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:20][CH2:19]3)=[C:14]([O:21][CH2:22][CH:23]3[CH2:25][CH2:24]3)[N:13]=2)=[O:11])[C:6](=[O:7])[NH:57][N:58]2[CH2:62][CH2:61][CH:60]([OH:63])[CH2:59]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 215389631-Aminopyrrolidin-3-olHCID 71087561HCID 71087561, compound

Product 1

HCID 71113060HCID 71113060, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-3-cyclopropyl-2-[(5-cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carbonyl)-amino]-propionic acid (100 mg, 0.29 mmol) in DMF (3 mL), was added TBTU (103 mg, 0.319 mmol), DIEA (249 μL, 1.45 mmol) and finally 1-amino-3-pyrrolidinol (CAN 887591-10-8, 30 mg, 0.29 mmol). The reaction mixture was stirred for 16 h at room temperature, concentrated in vacuo and purified by flash chromatography (silica gel, 10 g, 0% to 20% methanol in dichloromethane) to give the title compound, an epimeric mixture of products, (90 mg, 72%) as white foam; LC-MS (UV peak area/ESI) 96%, 429.2493 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by flash chromatography (silica gel, 10 g, 0% to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-671acf9a2c3544199c7fe87650b1d911
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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