Decylamine → HCID 58606950, compound

HRID 1744733Notes

Reaction equation

HRID 1744733 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15]([NH2:25])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(N(CC)C(C)C)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:15]([NH:25][C:12]([C@@H:9]1[CH2:10][CH2:11][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:14])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 8916DecylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 2734495(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acid

Product 1

HCID 58606950HCID 58606950, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)-(S)-(−)-2-azetidinecarboxylic acid (1) (90 mg; 0.447 mmol) is dissolved in methylene chloride (3 mL) at ambient temperature. n-Decylamine (72 mg; 0.470 mmol), N,N-diisopropylethylamine (116 mg; 0.895 mmol) and PyBOP (244 mg; 0.470 mmol) are added sequentially. The reaction is stirred for 4 days at room temperature, then concentrated under reduced pressure. The crude product is purified via silica gel chromatography using a gradient elution (10%→60% ethyl acetate in hexanes) affording the desired product (285). ISMS: MH+ 341.4

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product is purified via silica gel chromatography
  3. washa gradient elution (10%→60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f9ed0cd912f3413ab797cd7eb17060a2
Source dataset
uspto-grants-2006_03
Patent number
US07018642B2

Reaction notes

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