Triethylamine → HCID 43401847, compound

HRID 1891268Notes

Reaction equation

HRID 1891268 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:21]1([NH2:24])[CH2:23][CH2:22]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.CCOC(C)=O.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][CH2:8][C:9]([NH:24][CH:21]2[CH2:23][CH2:22]2)=[O:11])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 2724699PyBOPHCID 28354373N-[(4-Bromophenyl)methyl]glycine

Product 1

HCID 43401847HCID 43401847, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To a suspension of 2-(4-bromobenzylamino)acetic acid (7H2) (109 mmol, 26.5 g) in dichloromethane (300 ml) was added triethylamine (326 mmol, 33.0 g), cyclopropylamine (7H3) (163 mmol, 9.30 g) and PyBOP (109 mmol, 56.5 g). The suspension was stirred at room temperature overnight before concentration and purification on silica eluting with EtOAc/MeOH 1:0 to 9:1 to give 2-(4-bromobenzylamino)-N-cyclopropylacetamide (7H4) 9.38 g (30.3%); 1H NMR (400 MHz, MeODd4) 7.57 (d, 2H) 7.34 (d, 2H) 4.13 (m, 2H) 3.63 (s, 2H) 2.68 (m 1H) 0.76 (m, 2H) 0.56 (m, 2H).

Sources & evidence

ORD record
ord-7910d7f7306b4ee59c5944fdde9c0e37
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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