Diisopropylethylamine → 4-nitro-N-[[1-(phenylmethyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester

HRID 393419Notes

Reaction equation

HRID 393419 reaction equation
[CH2:1]([C:8]1([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18](=[O:31])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)[NH2:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:16][O:17][C:18](=[O:31])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)[NH:20][C:13]([C:8]1([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:15]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 74082814-Nitro-L-phenylalanine methyl esterHCID 226601311-Benzylcyclopentane-1-carboxylic acid

Product 1

HCID 542617434-nitro-N-[[1-(phenylmethyl)cyclopentyl]carbonyl]-L-phenylalanine methyl esterYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-benzylcyclopentane carboxylic acid (0.135 g, 0.66 mmol), 4-nitro-L-phenylalanine methyl ester (0.187 g, 0.72 mmol), and HBTU (0.272 g, 0.72 mmol) in 2 mL of DMF was treated with diisopropylethylamine (0.35 mL, 2 mmol). The mixture was stirred over night, concentrated, diluted with ethyl acetate, washed with water, 1 N HCl, water, saturated NaHCO3 and dried (MgSO4). The residue obtained after evaporation was purified by chromatography over 30 g of silica gel, eluting with 40% ethyl acetate:hexane to give 4-nitro-N-[[1-(phenylmethyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester (194 mg, 71%), as a white foam.

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with water, 1 N HCl, water, saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. customThe residue obtained
  6. customafter evaporation
  7. customwas purified by chromatography over 30 g of silica gel
  8. washeluting with 40% ethyl acetate

Sources & evidence

ORD record
ord-9f79534f44f44675a02610b5542cdfb0
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

Loading…