Diisopropylethylamine → HCID 86591596, compound

HRID 720816Notes

Reaction equation

HRID 720816 reaction equation
C(N(C(C)C)CC)(C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][CH2:17][CH2:18][CH2:19][OH:20].Cl[C:22](OC1C=CC([N+]([O-])=O)=CC=1)=[O:23].[NH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>CN(C)C=O.ClCCl.C(OCC)(=O)C>[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][CH2:17][CH2:18][CH2:19][O:20][C:22]([NH:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:23]

Participants

8

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 151417Glycine tert-butyl esterHCID 114124793-((Pyridin-2-yl)amino)propan-1-ol

Product 1

HCID 86591596HCID 86591596, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.6 ml of diisopropylethylamine are added to a solution of 0.9 g of 3-(pyridin-2-ylamino)propan-1-ol in 3 ml of N,N-dimethylformamide. This solution is subsequently added dropwise to a solution of 1 g of 4-nitrophenyl chloroformate in 10 ml of dichloromethane. After the mixture has been stirred at room temperature for 1 hour, 0.7 g of tert-butyl aminoacetate and 0.8 ml of DIPEA are added, and the mixture is stirred for a further 2 hours. Conventional work-up gives tert-butyl [3-(pyridin-2-ylamino)propoxycarbonylamino]acetate, Rf=0.488 (ethyl acetate).

Workup

  1. stirringthe mixture is stirred for a further 2 hours

Sources & evidence

ORD record
ord-5ecae82c28364910b621791158732cc8
Source dataset
uspto-grants-2006_11
Patent number
US07135587B2

Reaction notes

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